Process for production of 1-aryl-5-(trifluoromethyl)-1H-tetrazoles
View Patent ↗The present invention relates to a process for producing an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2): the process comprising the step of reacting in an organic solvent a tertiary amine, a 2,2,2-trifluoro-N-arylacetamide represented by Formula (1): and at least one member selected from the group consisting of phosphorus oxychloride and diphenyl chlorophosphate; and a process for producing a 1-aryl-5-(trifluoromethyl)-1H-tetrazole represented by Formula (4): the process comprising the step of reacting in an aromatic hydrocarbon solvent, in the presence of an amine salt, an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2) shown above and an azide.
1. A process for producing an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2):
wherein R is an aryl group optionally having one substituent,
the process comprising the step of reacting in an organic solvent a tertiary amine, a 2,2,2-trifluoro-N-arylacetamide represented by Formula (1):
wherein R is as defined above, and at least one member selected from the group consisting of phosphorus oxychloride and diphenyl chlorophosphate.
2. The process according to claim 1 , wherein R is a phenyl, methylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromophenyl, iodophenyl, or naphthyl group.
3. The process according to claim 1 , wherein the tertiary amine is triethylamine.
4. A process for producing a 1-aryl-5-(trifluoromethyl)-1H-tetrazole represented by Formula (4):
wherein R is an aryl group optionally having one substituent,
the process comprising the step of reacting in an aromatic hydrocarbon solvent, in the presence of an amine salt, an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2):
wherein R is as defined above, and an azide represented by Formula (3):
M(N 3 ) n (3)
wherein M is an alkali metal or alkaline-earth metal, and n is 1 or 2.
5. The process according to claim 4 , wherein R is a phenyl, methylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromophenyl, iodophenyl, or naphthyl group.
6. The process according to claim 4 , wherein the azide is sodium azide.
7. The process according to claim 4 , wherein the amine salt is triethylamine hydrochloride.
8. The process according to claim 4 , wherein the aromatic hydrocarbon solvent is at least one member selected from the group consisting of toluene and xylene.