Cyanamide → 5-tert-Butyl-1,3-thiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,3-dimethylbutanal (Aldrich, 5.0 g, 50 mmol), pyrrolidine (Aldrich, 4.4 mL, 52 mmol) and p-toluenesulfonic acid monohydrate (10 mg) in cyclohexane (70 mL) was heated to reflux for 3 hours under a Dean-Stark trap. The reaction mixture was decanted and concentrated under reduced pressure. The residue was dissolved in methanol (20 mL) and then cooled to 0° C. To this solution was added sulfur (Aldrich, 1.6 g, 50 mmol) and a solution of cyanamide (Aldrich, 2.1 g, 50 mmol) in methanol (5 mL). The reaction mixture was stirred at room temperature for 12 hours and was concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 2% methanol in dichloromethane to afford the title compound. MS (ESI+) m/z 157 (M+H)+.

Provenance & Evidence