Claims
- 1. A method of preparing 4-nitroisoxazoles which comprises the step of contacting an alpha-nitroketone corresponding to the formula: ##STR5## where R.sub.1 is an alkyl group having from 1 to 30 carbon atoms with a hydroximyl halide corresponding to the formula: ##STR6## where R is an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkanoyl group having 2 to 20 carbon atoms or an aroyl group having 7 to 20 carbon atoms and where X is chlorine, bromine, iodine or fluorine in the presence of a tertiary amine corresponding to the formula: ##STR7## where R.sub.3, R.sub.4 and R.sub.5 are alkyl, cycloalkyl or aryl groups or where R.sub.3, R.sub.4 and or R.sub.5 together with N are heterocyclic, where R.sub.3, R.sub.4 and R.sub.5 groups have 1 to 12 carbon atoms and where the sum of R.sub.3, R.sub.4 and R.sub.5 is 3 to 36 carbon atoms or tetraalkyl substituted C.sub.2 and C.sub.5 alkylene diamines and tetraalkyl substituted guanidines, where the tetraalkyl groups have 1 to 6 carbon atoms at a temperature of from about -10.degree. to 50.degree. C., wherein the mole ratio of said hydroximyl halide to said nitroketone is between about 1:1 and 1:5.
- 2. A method according to claim 1 wherein said nitroketone is 1-nitro-2-hexanone.
- 3. A method according to claim 1 wherein said nitroketone is 1-nitro-2-decanone.
- 4. A method according to claim 1 wherein said nitroketone is 1-nitro-2-dodecanone.
- 5. A method according to claim 1 wherein said nitroketone is 1-nitro-2-tetradecanone.
- 6. A method according to claim 1 wherein said nitroketone is 1-nitro-2-hexadecanone.
- 7. A method according to claim 1 wherein said hydroximyl halide is tridecanoylhydroximyl chloride.
- 8. A method according to claim 1 wherein said hydroximyl halide is phenylhydroximyl chloride.
- 9. A method according to claim 1 wherein said hydroximyl halide is phenacylhydroximyl chloride.
- 10. A method according to claim 1 wherein said hydroximyl halide is pentadecanoylhydroximyl chloride.
- 11. A method according to claim 1 wherein said hydroximyl halide is acetylhydroximyl chloride.
- 12. A method according to claim 1 wherein said tertiary amine is a trialkylamine, wherein said alkyl groups have from 1 to 12 carbon atoms.
- 13. A method according to claim 1 wherein said tertiary amine is triethylamine.
- 14. A method according to claim 1 wherein said tertiary amine is diethylmethylamine.
- 15. A method of preparing 4-nitroisoxazoles which comprises the step of contacting an alpha-nitroketone corresponding to the formula: ##STR8## where R.sub.1 is an alkyl group having from 1 to 30 carbon atoms with a hydroximyl halide corresponding to the formula: ##STR9## where R is an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkanoyl group having 2 to 20 carbon atoms or an aroyl group having 7 to 20 carbon atoms and where X is chlorine, bromine, iodine or fluorine in the presence of tetramethyl guanidine at a temperature of from about -10.degree. to 50.degree. C. wherein the mole ratio of said hydroximyl halide to said nitroketone is between about 1:1 and 1:5.
- 16. A method of preparing 4-nitroisoxazoles which comprises the step of contacting an alpha-nitroketone corresponding to the formula: ##STR10## where R.sub.1 is an alkyl group having from 1 to 30 carbon atoms with a hydroximyl halide corresponding to the formula: ##STR11## where R is an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkanoyl group having 2 to 20 carbon atoms or an aroyl group having 7 to 20 carbon atoms and where X is chlorine, bromine, iodine or fluorine in the presence of pyridine at a temperature of from about -10.degree. to 50.degree. C. wherein the mole ratio of said hydroximyl halide to said nitroketone is between about 1:1 and 1:5.
- 17. A method according to claim 1 wherein said contacting is conducted in the presence of a reaction inert organic solvent having a boiling point between about 30.degree. and 100.degree. C.
- 18. A method of preparing 4-nitroisoxazoles which comprises the step of contacting an alpha-nitroketone corresponding to the formula: ##STR12## where R.sub.1 is an alkyl group having from 1 to 30 carbon atoms with a hydroximyl halide corresponding to the formula: ##STR13## where R is an alkanoyl group having 2 to 20 carbon atoms or an aroyl group having 7 to 20 carbon atoms and where X is chlorine, bromine, iodine or fluorine in the presence of a tertiary amine having 3 to 36 carbon atoms, wherein said amine is a tetraalkyl substituted C.sub.2 to C.sub.5 alkylene diamine, a C.sub.1 to C.sub.6 tetraalkyl substituted guanidine, N,N-dimethylaniline, N,N-dimethylbenzylamine, N-ethyldibenzylamine, tricyclohexylamine, pyridine, methylpiperidine, 2-ethylpyridine, 1,4-dimethylpiperazine, 4-ethylpyridine, 2,4-ludidine, 3-picoline, 2,4,6-trimethylpyridine or quinoline at a temperature of from about -10.degree. to 50.degree. C. wherein the mole ratio of said hydroximyl halide to said nitroketone is between about 1:1 and 1:5.
CROSS REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of our copending application Ser. No. 685,250 filed May 11, 1976 now abandoned.
US Referenced Citations (7)
Non-Patent Literature Citations (2)
Entry |
"Heterocyclic Compounds", (isoxazoles), Interscience, (1962), p. 19. |
Morrison et al., "Organic Chemistry", (1966), pp. 854, 870, 1075. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
685250 |
May 1976 |
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