Acetonitrile → HCID 53726410, compound

Temperature

50 °C

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.

1. customTo a 250 mL, 3-necked flask fitted with a mechanical stirrer
2. customprecipitated
3. customrose to about 50° C
4. temperatureThe contents were gently refluxed for one hour during which the color
5. temperatureAfter cooling
6. extractionThe mixture was extracted with ether (2 ×100 mL)
7. washwashed with 10% HCl (25 mL)
8. concentrationAfter concentration
9. customdrying at 1 mm vacuum overnight

ORD record

ord-a2803b8b3ff04e8a802ee50df6494f62

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05880288