Sodium Cyanide → HCID 67326339, compound

Participants

Reaction Conditions

Reaction Steps

Sodium cyanide (124 mg, 2.53 mmol) was added to a solution of dimethylamine hydrochloride (280 mg, 3.43 mmol) in water (10 mL), followed by the addition of a solution of 4-phenylthiazole-2-carbaldehyde (400 mg, 2.11 mmol) in methanol (20 mL) while maintaining the temperature at −25° C. The reaction mixture was further stirred for 4 h at same temperature, then it was diluted with water and the organic product was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to get the crude product, which was purified by column chromatography (silica 60-120 mesh, eluant 15% EtOAc in petroleum ether), to yield 2-(dimethylamino)-2-(4-phenylthiazol-2-yl)acetonitrile (160 mg, yield 31%). 1H NMR (400 MHz, CDCl3) δ 7.97-7.94 (m, 2H), 7.57 (s, 1H), 7.46-7.42 (m, 2H), 7.38-7.33 (m, 1H), 5.12 (s, 1H), 2.50 (s, 6H). MS (ESI) m/z: Calculated for C13H13N3S: 243.08. found: 244.2 (M+H)+.

Provenance & Evidence