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

Temperature

0 °C

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)+.

1. temperaturewas heated
2. temperatureto reflux for 3 hours under a Dean-Stark trap
3. customThe reaction mixture was decanted
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in methanol (20 mL)
6. concentrationwas concentrated under reduced pressure
7. customThe residue was purified by column chromatography (SiO2, 2% methanol in dichloromethane

ORD record

ord-869e6ed1327e4c8ea2939ac889e76093

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006275B2