Chloroacetyl chloride → N'-(Chloroacetyl)-2,2,2-trifluoroacetohydrazide

Participants

Reaction Conditions

Reaction Steps

Hydrazine hydrate (15 g, 35 wt %) is mixed acetonitrile (22.5 mL) and cooled to about 10° C. Ethyl trifluoroacetate (23.3 g) is added over 1 hour. The resulting solution is warmed to 20° C. and stirred for about 1 hour. The solution is cooled to 0-2° C. 50 wt % aqueous NaOH (7.88 g) and chloroacetyl chloride (22.2 g) are added to the reaction solution simultaneously over 2 hours. The reaction mixture is warmed to 15-18° C. and stirred for about 5 hours. Solvent is distilled off under vacuum at about 30° C. Water (50 mL) and ethyl acetate (100 mL) are added to the obtained crude. The organic and aqueous layers are separated and aqueous layer is washed with ethyl acetate (2×50 mL). The organic layers are combined and washed with water (2×50 mL) followed by washing with 15% sodium chloride solution (2×50 mL). The combined organic layer is dried over sodium sulfate. The solvent is completely distilled off under vacuum to afford the title compound. (Yield: 98.3%)

Provenance & Evidence