Dimethylformamide → HCID 21643578, compound

Participants

Reaction Conditions

Reaction Steps

Dry DMF (20 ml, 0.255 mol) was cooled to 0-5° C. with an ice/water bath. Phosphorus oxychloride (20 ml, 0.215 mol) was added dropwise over 0.5 h. 2-(3-pyridyl)thiazol-4-ol (hybromide salt, 13 g, 0.05 mol) was added in one portion and the reaction mixture was heated to 110° C. for 15 min. After cooling the reaction mixture was poured on ice water and neutralized with solid potassium carbonate. The precipitate was filtered, washed with water, once with ethanol, and dried to dryness to get 4-chloro-2-(3-pyridyl)thiazole-5-carbaldehyde as brown solid. 1H NMR (300 Mz, DMSO-d6): δ: 10.00 (s, 1H), 9.21 (d, 1H, J=1.2 Hz), 8.78 (dd, 1H, J=1.5 Hz), 8.42 (d, 1H, J=7.2 Hz), 7.60 (m, 1H). MS(ESI): 255, 257 (M+MeOH).

Provenance & Evidence