Acetamide → HCID 68005829, compound

A solution of ethyl 3,3-bis(methylthio)-2-cyanoacrylate (10.0 g, 45.6 mmol), acetamide (3.0 g, 50.2 mmol), sodium hydride (70% oil, 2.0 g, 58.3 mmol) in ethyl acetate (250 mL)-toluene (250 mL) was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed successively with water and brine, and dried over anhydrous sodium sulfate. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue were added ethanol (200 mL), and the mixture was stirred with heating under reflux for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with diethyl ether to give the title compound (4.1 g, 39%) as a pale-yellow powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure, water
2. additionwas added to the residue
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed successively with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe insoluble material was removed by filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. additionTo the residue were added ethanol (200 mL)
9. temperaturewith heating
10. temperatureunder reflux for 16 hr
11. concentrationThe reaction mixture was concentrated under reduced pressure
12. washthe residue was washed with diethyl ether

ORD record

ord-071fb064d8064d0ab6e1c58e17a728c4

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614208B2