Thionyl Chloride → N-(1-methoxy-2,2,2-trichloroethyl)nicotinamide

150 ml of benzene was added to 10.0 g of N-(1-hydroxy-2,2,2-trichloroethyl)nicotinamide. 5.3 g of thionyl chloride was added dropwise thereto and the mixture was heated under reflux (60° to 80° C.) for about 5 h under stirring to complete the production of N-(1,2,2,2-tetrachloroethyl)nicotinamide. The reaction liquid was cooled to 30° C. or below. 20 ml of methanol was added to the liquid. 4.0 g of triethylamine was added dropwise to the liquid mixture while it was kept at 5° C. and the obtained mixture was stirred at room temperature for 3 h. Then, the mixture was kept at room temperature overnight. The reaction liquid was poured in an aqueous sodium bicarbonate solution and a benzene layer thus separated was washed with saturated aqueous common salt solution and water and dried over anhydrous sodium sulfate. After concentration, the residue was recrystallized from methanol to obtain 4.8 g of N-(1-methoxy-2,2,2-trichloroethyl)nicotinamide.

1. temperaturethe mixture was heated
2. temperatureunder reflux (60° to 80° C.) for about 5 h
3. customThe reaction liquid
4. temperaturewas cooled to 30° C. or below
5. customwas kept at 5° C.
6. stirringthe obtained mixture was stirred at room temperature for 3 h
7. customThe reaction liquid
8. customa benzene layer thus separated
9. washwas washed with saturated aqueous common salt solution and water
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationAfter concentration
12. customthe residue was recrystallized from methanol

ORD record

ord-b386df8ab5ad45a9b76eb7c868224d34

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04659722