CA2348749A1 - Process for preparing triazines using a combination of lewis acids and reaction promoters - Google Patents

Process for preparing triazines using a combination of lewis acids and reaction promoters Download PDF

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CA2348749A1
CA2348749A1 CA002348749A CA2348749A CA2348749A1 CA 2348749 A1 CA2348749 A1 CA 2348749A1 CA 002348749 A CA002348749 A CA 002348749A CA 2348749 A CA2348749 A CA 2348749A CA 2348749 A1 CA2348749 A1 CA 2348749A1
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carbon atoms
compound
formula
halide
reaction
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CA2348749C (en
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Ram B. Gupta
Dennis J. Jakiela
Sampath Venimadhavan
Russell C. Cappadona
Venkatrao K. Pai
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Cytec Technology Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Artificial Filaments (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

It has been now surprisingly discovered after extensive research that 2-halo - 4,6-bisaryl-1,3,5-triazine can be prepared with unprecedented selectivity, efficiency, mild conditions, and in high yield by the reaction of cyanuric halide with aromatics in the presence of at least one Lewis acid and at leas t one reaction promoter. This reaction is also unprecedently general as a variety of aromatics can be used to produce a wide selection of 2-halo-4,6- bisaryl-1,3,5-triazines. The novel approach includes the use of the reaction promoters in combination with at least one Lewis acid under certain reaction conditions to promote the formation of 2-halo-4,6-bisaryl-1,3,5-triazine compounds from cyanuric halide. Preferably, the Lewis acids and reaction promoters are combined to form a complex. 2-halo-4,6-bisaryl-1,3,5-triazines are key intermediates for making 2-(2-oxyaryl)-4,6-bisarly-1,3,5-triazine class of UV absorbers.

Claims (31)

1. A process for synthesizing a triazine compound of Formula III:
wherein X is a halogen and Ar1 and Ar2 are the same or different and each is a radical of a compound of Formula I1:
wherein R6, R7, R8, R9, and R10 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R6 and R7, R7 and R8, R8 and R9, or R9 and R10, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, which comprises:
reacting a cyanuric halide of the Formula V:

where each X is independently a halide such as fluorine, chlorine, bromine or iodine, with at least one compound of Formula II with the reaction being conducted in the presence of a reaction facilitator comprising sufficient amounts of at least one Lewis acid and at least one reaction promoter for a sufficient time at a suitable temperature and pressure, optionally in the presence of at least one solvent, to produce a triazine compound of Formula III, with the proviso that said reaction promoter is different from the compound of Formula II.
2. A process for synthesizing a triazine compound of the Formula I:
which comprises the following steps:
(i) reacting a cyanuric halide of the Formula V:
where each X is independently a halide such as fluorine, chlorine, bromine or iodine, with at least one compound of Formula II:

wherein R6, R7, R8, R9 and R10 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R6 and R7, R7 and R8, R8 and R9, or R9 and R10, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, with the reaction being conducted in the presence of a reaction facilitator comprising sufficient amounts of at least one first Lewis acid and at least one first reaction promoter for a sufficient time at a suitable temperature and pressure, optionally in the presence of at least one solvent, to produce a triazine compound of Formula III:
wherein X is a halogen and Ar1 and Ar2 are the same or different and each is a radical of a compound of Formula II; and (ii) reacting a compound of Formula III with a compound of Formula IV:

wherein R1, R2, R3, R4, and R5 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, cycloalkyl of 5 to 25 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbons atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, optionally with either of R3 and R4, or R4 and R5, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, and Y is a direct bond, O, NR", or SR" wherein R" is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, for a sufficient time, at a suitable temperature and pressure, optionally in the presence of a second Lewis acid, a second reaction promoter, to form the compound of Formula I, with the proviso that: (1) said reaction promoter is different from the reactant which is reacting in that step, and (2) that the compound of Formula II is different from the compound of Formula IV.
3. The process of claim 2 wherein the reaction to form the compound of Formula III and the reaction to form the compound of Formula I are carried out without isolating the compound of Formula III.
4. The process of claim 1 wherein the Lewis acid is aluminum halide, boron halide, tin halide, zinc halide, lead halide, manganese halide, magnesium halide, copper halide, titanium halide, alkyl aluminum halide, gallium halide, iron halide, arsenic halide, antimony halide, or a mixture thereof, and is present in an amount of about 1 to about 10 mol equivalents to the cyanuric halide.
5. The process of claim 1 wherein the Lewis acid catalyst is aluminum chloride, aluminum bromide, boron trifluoride, tin chloride, zinc chloride, titanium tetrachloride, or a mixture thereof.
6. The process of claim 1 wherein the reaction promoter is an acid, base, water, alcohol, aliphatic halide, halide salt, acid halide, halogen, alkene, alkyne, ester, anhydride, carbonate, urethane, carbonyl, epoxy, ether or acetal compound or a mixture thereof, and is present in an amount of about 0.01 to 5 mol equivalents to the cyanuric halide.
7. The process of claim 1 wherein the solvent is heptane, carbon disulfide, cyclohexane, chlorobenzene, dichlorobenzene, trichlorobenzene, bromobenzene, dibromobenzene, tribromobenzene, toluene, xylene, trimethylbenzene, nitrobenzene, dinitrobenzene, anisole, nitroalkanes, heptane, cyclohexane, benzene, nitrobenzene, dinitrobenzene, toluene, xylene, 1,1,2,2-tetrachloroethane, dichloromethane, dichloroethane, ether, dioxane, tetrahydrofuran, benzonitriles, dimethylsulfoxide, tetramethylene sulfone, carbon disulfide, and benzene rings substituted with at least one halide including chlorobenzene, dichlorobenzene, trichlorobenzene, fluorobenzene, difluorobenzene, trifluorobenzene, bromobenzene, dibromobenzene, tribromobenzene, or mixtures thereof.
8. The process of claim 1 which further comprises forming a mixture of the reaction facilitator and a portion of the solvent before combining the mixture with the cyanuric halide of Formula V and the compound of Formula II.
9. The process of claim 8 which further comprises forming a mixture of the cyanuric halide, aromatic compound; and a portion of the solvent before adding the reaction facilitator mixture to the mixture.
10. The process of claim 1 wherein the compound of Formula II is added between about 5 minutes to 15 hours and at a temperature between about -50°C to about 150°C and the reaction time is between about 10 minutes to about 48 hours and at a temperature between about -50°C to about 150°C.
11. The process of claim 2 wherein the compound of Formula IV is added between about 5 minutes to 10 hours and at a temperature between about 0°C to about 100°C and the reaction time is between about 30 minutes to about 24 hours and at a temperature between about 20°C to about 150°C.
12. The process of claim 2 wherein step (i) is performed prior to step (ii) further comprising adding a second Lewis acid and a second reaction promoter along with the compound of Formula IV to react with the compound of Formula III.
13. The process of claim 2 wherein the steps are performed simultaneously and continuously.
14. The process of claim 12 wherein the second Lewis acid is the same as the first Lewis acid, and the second reaction promoter is the same as the first reaction promoter.
15. The process of claim 1 wherein the Lewis acid is mixed with the compound of Formula V prior to adding the reaction promoter.
16. The process of claim 1 wherein the Lewis acid is mixed with the compound of Formula II prior to adding the second reaction promoter.
17 The process of claim 2 wherein the second Lewis acid is mixed with the compound of Formula III prior to adding the second reaction promoter.
18. The process of claim 2 wherein the second Lewis acid is mixed with the compound of Formula IV prior to adding the second reaction promoter.
19. The process of claim 1 wherein the reaction promoter is mixed with the compound of Formula V prior to adding the Lewis acid.
20. The process of claim 1 wherein the reaction promoter is mixed with the compound of Formula II prior to adding the Lewis acid.
21. The process of claim 2 wherein the second reaction promoter is mixed with the compound of Formula III prior to adding; with the second Lewis acid.
22. The process of claim 2 wherein the second reaction promoter is mixed with the compound of Formula IV prior to adding the second Lewis acid.
23. The process of claim 2 wherein the compound of Formula III and IV are mixed prior to adding either the second reaction promoter or second Lewis acid.
24. A process for synthesizing a triazine compound of Formula I:
wherein Ar1 and Ar2 are the same or different, and each independently is a radical of a compound of Formula II:
wherein R6, R7, R8, R9, and R10 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R6 and R7, R7 and R8, R8 and R9, or R9 and R10, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, which comprises:
simultaneously reacting in the presence of a reaction facilitator comprising at least one Lewis acid and at least one reaction promoter, sufficient amounts of a cyanuric halide of Formula V:

where each X is independently a halide such as fluorine, chlorine, bromine or iodine, with a compound of Formula IV:
wherein R1, R2, R3, R4, and R5 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, cycloalkyl of 5 to
25 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbons atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, optionally with either of R3 and R4, or R4 and R5, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, and Y is a direct bond, O, NR", or SR" wherein R" is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and a compound of Formula II:

wherein R6, R7, R8, R9, and R10 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R6 and R7, R7 and R8, R8 and R9, or R9 and R10, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, for a sufficient time, at a suitable temperature and pressure, optionally in the presence of at least one solvent, to form the compound of Formula I, with the proviso that: (1) said reaction promoter is different from the reactant which is reacting in that step, and (2) the compound of Formula II is different from the compound of Formula IV.
25. A process for synthesizing a triazine compound of Formula I:
wherein Ar1 and Ar2 are the same or different, and each independently is a radical of a compound of Formula II:

wherein R6, R7, R8, R9, and R10 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R6 and R7, R, and R8, R8 and R9, or R9 and R10, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, which comprises:
reacting in the presence of a reaction facilitator comprising at least one Lewis acid and at least one reaction promoter, sufficient amounts of a compound of Formula III:

wherein X is independently a halide such as fluorine, chlorine, bromine or iodine and Ar1 and Ar, arc the same or different and each is a radical of a compound of Formula II; with a compound of Formula IV:

wherein R1, R2, R3, R4,and R5 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, cycloalkyl of 5 to 25 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbons atoms, OR, NRR', CONRR', OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R' are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, optionally with either of R3 and R4, or R4 and R5, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, and Y is a direct bond, O, NR", or SR" wherein R" is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, for a sufficient time, at a suitable temperature and pressure, optionally in the presence of at least one solvent, to form the compound of Formula I, with the proviso that:
(I) said reaction promoter is different from the compound of Formula IV, and (2) the compound of Formula II is different from the compound of Formula IV.
26. A triazine compound formation reaction facilitator comprising:
at least one Lewis acid; and at least one reaction promoter in an amount sufficient to synthesize triazine compounds at lower reaction temperatures, greater yields, or higher selectivities compared to at least one Lewis acid alone.
27. The reaction facilitator of claim 26 wherein the Lewis acid is present in an amount between about 0.5 to about 500 mol equivalents to the reaction promoter.
28. The reaction facilitator of claim 26 wherein the Lewis acid is aluminum halide, boron halide, tin halide, zinc halide, lead halide, manganese halide, magnesium halide, copper halide, titanium halide, alkyl aluminum halide, gallium halide, iron halide, arsenic halide, antimony halide, or a mixture thereof, and the reaction promoter is an acid, base, water, alcohol, aliphatic halide, halide salt, acid halide, halogen, alkene, alkyne, ester, anhydride, carbonate, urethane, carbonyl, epoxy, ether or acetal compound, or a mixture thereof.
29. The reaction facilitator of claim 26 in the form of a complex and further comprising a solvent.
30. A complex composition comprising the reaction facilitator of claim 26 and cyanuric halide of Formula V.
31. A complex composition comprising the reaction facilitator of claim 26 and 2-halo-4,6-bisaryl-1,3,5-triazine of Formula III.
CA2348749A 1998-11-17 1999-11-17 Process for preparing triazines using a combination of lewis acids and reaction promoters Expired - Lifetime CA2348749C (en)

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US10878698P 1998-11-17 1998-11-17
US60/108,786 1998-11-17
PCT/US1999/027253 WO2000029392A1 (en) 1998-11-17 1999-11-17 Process for preparing triazines using a combination of lewis acids and reaction promoters

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