Sodium hydride → HCID 19896206, compound

Participants

Reaction Conditions

Reaction Steps

A 20 ml dimethylformamide solution of 2.7 g of ethyl 3-amino-4,4,4-trifluorocrotonate was added dropwise to a 20 ml dimethylformamide solution of 0.78 g of sodium hydride (purity: 55%) with stirring at 0° C. After heated to room temperature under stirring for 15 minutes, the mixed solution was cooled to -30° C. and then added dropwise with 20 ml of a dimethylformamide solution of 3.8 g of 2,6-dichloro-4-trifluoromethylphenyl isocyanate. The resulting solution was again heated to room temperature and stirred at 80° C. for 30 minutes. Then the solvent was distilled away under reduced pressure and the residue was dissolved by adding 100 ml of water. This aqueous solution was washed twice with diethyl ether, then added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid, and extracted with ethyl acetate. The obtained organic layer was washed with water and dried, and the solvent was distilled away under reduced pressure to obtain 3.75 g of a crude product. This crude product was recrystallized from a mixed solvent of diisopropyl ether and isopropyl alcohol to obtain 1.65 g of the objective compound.

Provenance & Evidence