Claims
- 1. A compound having the formula (II): whereinW is nitrogen or —CR4; R2, R4, R5 and R6 are independently selected from hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n—, nitro, cyano and —SF5; R3 is hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n—, nitro, cyano, —SF5, or phenyl substituted by one to five members of the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n—, nitro, cyano and —SF5, which are the same or different; R7 is C1-6 alkyl or C1-6 haloalkyl; and n is 0, 1 or 2.
- 2. A compound according to claim 1, having one or more of the following features:R2 is halogen or hydrogen; R3 represents halogen, C1-6 haloalkyl, C1-6 haloalkoxy, R7S(O)p—, —SF5, or phenyl substituted by one to three members of the group consisting of trifluoromethyl, trifluoromethoxy, difluoromethyl, —S(O)nCF3, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethoxy, dichlorofluoromethoxy and halogen, which are the same or different; R4 is halogen; R5 and R6 are hydrogen.
- 3. The compound according to claim 1, which is 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)succinonitrile.
- 4. A process for the preparation of a compound of formula (II) as defined in claim 1, said process comprising oxidizing a compound having the formula (III): wherein W, R2, R3, R5 and R6 are as defined in claim 1, with an oxidant.
- 5. A process according to claim 4, wherein the compound of formula (III) has one or more of the following features:R2 is halogen or hydrogen; R3 represents halogen, C1-6 haloalkyl, C1-6 haloalkoxy, R7S(O)p—, —SF5, or phenyl substituted by one to three members of the group consisting of trifluoromethyl, trifluoromethoxy, difluoromethyl, —S(O)nCF3, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethoxy, dichlorofluoromethoxy and halogen, which are the same or different; R4 is halogen; R5 and R6 are hydrogen.
- 6. A process according to claim 4, wherein the oxidant is selected from a quinone; a peroxide; a hypohalite; an alkali metal hydroxide in the presence of air; a metal salt; and a metal oxide.
- 7. A process according to claim 4, comprising oxidizing 2-(2,6-dichloro-4-trifluoromethylphenylhydrazino)succinonitrile, with an oxidant, to afford 2-(2,6-dichloro-4-trifluoromethylphenylhydrazino)succinonitrile.
- 8. A process according to claim 7, wherein the oxidant is cupric chloride.
- 9. A process for the preparation of a compound of formula (II) as defined in claim 1, said process comprising reacting an enolate salt of a compound having the formula (IV): with a diazonium salt having the formula (V): wherein W, R2, R3, R5 and R6 are as defined in claim 1 and X is hydrogen sulfate or chloride.
- 10. A process according to claim 9, wherein the compound of formula (V) has one or more of the following features:R2 is halogen or hydrogen; R3 represents halogen, C1-6 haloalkyl, C1-6 haloalkoxy, R7S(O)p—, —SF5, or phenyl substituted by one to three members of the group consisting of trifluoromethyl, trifluoromethoxy, difluoromethyl, —S(O)nCF3, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethoxy, dichlorofluoromethoxy and halogen, which are the same or different; R4 is halogen; R5 and R6 are hydrogen.
- 11. A process according to claim 9, wherein the diazonium salt of formula (V) is prepared in situ by diazotizing the corresponding compound of the formula (Va): wherein W, R2, R3, R5 and R6 are as defined in claim 9.
- 12. A process according to claim 11, wherein the compound of formula (Va) is 2,6-dichloro-4-trifluoromethylphenylalanine.
- 13. A compound having the formula (III): wherein W is nitrogen or —CR4;R2, R4, R5 and R6 are independently selected from hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n—, nitro, cyano and —SF5; R3 is hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n—, nitro, cyano, —SF5, or phenyl substituted by one to five members of the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n—, nitro, cyano and —SF5, which are the same or different; R7 is C1-6 alkyl or C1-6 haloalkyl; and n is 0, 1 or 2.
- 14. A compound according to claim 13, having one or more of the following features:R2 is halogen or hydrogen; R3 represents halogen, C1-6 haloalkyl, C1-6 haloalkoxy, R7S(O)p—, —SF5, or phenyl substituted by one to three members of the group consisting of trifluoromethyl, trifluoromethoxy, difluoromethyl, —S(O)nCF3, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethoxy, dichlorofluoromethoxy and halogen, which are the same or different; R4 is halogen; R5 and R6 are hydrogen.
- 15. The compound according to claim 13, which is 2,6-dichloro-4-trifluoromethylphenylhydrazine.
- 16. A process for the preparation of a compound of formula (III) as defined in claim 13, said process comprising reacting an arylhydrazine having the formula (VII): wherein W, R2, R3, R5 and R6 are as defined in claim 13, with a compound of formula (VIII):CH(CH)═CH(CN) (VIII).
- 17. A process according to claim 16, wherein the compound of formula (VII) has one or more of the following features:R2 is halogen or hydrogen; R3 represents halogen, C1-6 haloalkyl, C1-6 haloalkoxy, R7S(O)p—, —SF5, or phenyl substituted by one to three members of the group consisting of trifluoromethyl, trifluoromethoxy, difluoromethyl, —S(O)nCF3, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethoxy, dichlorofluoromethoxy and halogen, which are the same or different; R4 is halogen; and R5 and R6 are hydrogen.
- 18. A process according to claim 16, comprising reacting 2-(2,6-dichloro-4-trifluoromethylphenylhydrazine with fumaronitrile to afford 2-(2,6-dichloro-4-trifluoromethylphenylhydrazino)succinonitrile.
Priority Claims (1)
Number |
Date |
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9705316 |
Mar 1997 |
GB |
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Parent Case Info
This application is a division of U.S. application Ser. No. 09/388,524, filed Sep. 2, 1999, now U.S. Pat. No. 6,084,105, incorporated by reference herein in its entirety and relied upon, which is a continuation of International Patent Application No. PCT/EP98/01057, filed Feb. 25, 1998, and designating the United States, incorporated by reference herein in its entirety and relied upon, which claims the priority of U.S. Provisional Patent Application No. 60/039,516, filed Mar. 3, 1997 and United Kingdom Patent Application No. 97 05316.9, filed Mar. 14, 1997.
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Provisional Applications (1)
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Number |
Date |
Country |
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60/039516 |
Mar 1997 |
US |
Continuations (1)
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Number |
Date |
Country |
Parent |
PCT/EP98/01057 |
Feb 1998 |
US |
Child |
09/388524 |
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US |