2-Methoxyethylamine → N-(2-methoxyethylamino-2,2,2-trichloroethyl)nicotinamide

150 ml of benzene was added to 5.0 g of N-(1-hydroxy-2,2,2-trichloroethyl)nicotinamide. 2.6 g of thionyl chloride was added dropwise to the mixture under stirring and the obtained mixture was heated under stirring at 60° to 80° C. for about 5 h to complete the production of N-(1,2,2,2-tetrachloroethyl)nicotinamide. The reaction solution was cooled to a temperature of 30° C. or below. 1.4 g of 2-methoxyethylamine was added thereto and then 3.7 g of triethylamine was added dropwise to the liquid mixture kept at 5° C. After stirring at room temperature for 3 h, the mixture was left to stand at room temperature overnight. The reaction solution was poured in an aqueous sodium bicarbonate solution. A benzene layer thus separated was washed with a saturated aqueous common salt solution and water and dried over anhydrous sodium sulfate. After concentration, the residue was recrystallized from a solvent mixture of n-hexane and ethyl acetate to obtain 2.5 g of N-(2-methoxyethylamino-2,2,2-trichloroethyl)nicotinamide. m.p. 75° to 77° C.

1. temperaturethe obtained mixture was heated
2. stirringunder stirring at 60° to 80° C. for about 5 h
3. temperatureThe reaction solution was cooled to a temperature of 30° C. or below
4. customkept at 5° C
5. stirringAfter stirring at room temperature for 3 h
6. waitthe mixture was left
7. customA benzene layer thus separated
8. washwas washed with a saturated aqueous common salt solution and water
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationAfter concentration
11. customthe residue was recrystallized from a solvent mixture of n-hexane and ethyl acetate

ORD record

ord-228489d045564f03a1dc20bb211301a1

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04659722