Acetonitrile → HCID 53726410, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL, 3-necked flask fitted with a mechanical stirrer, thermometer, and a reflux condenser, was charged thioacetamide (9.02 g, 0.12 mol) and 60 mL acetonitrile. To this solution was added ethyl 2-chloro-4,4,4-trifluoroacetoacetate (21.86 g, 0.10 mol) dropwise over a period of 15 minutes. A slight exotherm occurred which raised the temperature to 50° C. The reaction mixture was stirred for two hours at room temperature during which time a yellow solid precipitated. Then triethylamine (35 mL, 0.25 mol) was added dropwise with the evolution of white fumes. The reaction temperature rose to about 50° C. The contents were gently refluxed for one hour during which the color changed from yellow to brown. After cooling, water (25 mL) was added. The mixture was extracted with ether (2 ×100 mL) and washed with 10% HCl (25 mL). After concentration and drying at 1 mm vacuum overnight, the desired compound was isolated as a brown solid, 22.15 g, a 90.6% yield with a 97.8 wt.% purity assay. m.p. 30°-32° C.

Provenance & Evidence