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

Temperature

10 °C

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%)

1. temperatureThe resulting solution is warmed to 20° C.
2. temperatureThe solution is cooled to 0-2° C
3. temperatureThe reaction mixture is warmed to 15-18° C.
4. stirringstirred for about 5 hours
5. distillationSolvent is distilled off under vacuum at about 30° C
6. additionWater (50 mL) and ethyl acetate (100 mL) are added to the
7. customobtained crude
8. customThe organic and aqueous layers are separated
9. washaqueous layer is washed with ethyl acetate (2×50 mL)
10. washwashed with water (2×50 mL)
11. washby washing with 15% sodium chloride solution (2×50 mL)
12. dry with materialThe combined organic layer is dried over sodium sulfate
13. distillationThe solvent is completely distilled off under vacuum

ORD record

ord-72f4624f34d74f78aafd161f013e511b

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309724B2