Cyanoacetamide → 2-Aminothiophene-3-carboxamide

Participants

Reaction Steps

Triethylamine (36 mL, 256 mmol) was added to the solution of 2-cyanoacetamide (10.8 g, 128 mmol) and [1,4]-dithiane-2,5-diol (19.5 g, 128 mmol) in ethanol (400 mL). The resulting reaction mixture was stirred at room temperature for 5 min, then heated at reflux for 2 h. After the reaction mixture is cooled to room temperature, it was filtered and concentrated under vacuum. The residue was then taken up into ethyl acetate (400 mL) and washed with aqueous sodium hydroxide (1 M, 1×200 mL), water (2×200 mL) and brine (1×200 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give the above titled compound as a light yellow solid (16 g, 113 mmol, 88% yield). LC-MS [M+H]+ m/z 143.

Provenance & Evidence