Difluoromethylation of a phenyl triazolinone

Details Difluoromethylation of a phenyl triazolinone Difluoromethylation of a phenyl triazolinone

1994-05-27

1995-08-01

Morris, Patricia L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D24912

Patent

active

054381495

ABSTRACT:
An improved process for the difluoromethylation of a 1-phenyl-1H-1,2,4-triazol-5-one at the 4-position of the triazole ring with chlorodifluoromethane significantly reduces the amount of base required for the process, thereby reducing the environmental impact of the process by reducing the amount of by-product salts in the waste stream. The improvement comprises reacting the triazolinone with potassium carbonate in a solvent such as dimethylformamide, at a carbonate to triazolinone ratio in the range of about 0.55 to 1.0; reducing the water content of the reaction mixture to below about 2400 ppm by distillation; heating the reaction mixture in a sealed autoclave to 110.degree. to 180.degree. C., adding a 10 to 15 percent molar excess of chlorodifluoromethane, heating the reaction mixture at a temperature of 140.degree. to 210.degree. C. for 5 to 60 minutes, and recovering the difluoromethylated triazolinone.

REFERENCES:
patent: 5125958 (1992-06-01), Halfon et al.

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