Sodium Bicarbonate → 5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-ylamine

Participants

Reaction Steps

To a 50 ml eggplant-shaped flask were added 0.50 g (1.69 mmol) 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 15 ml dichloromethane, and then added dropwise 2.9 ml (5.06 mmol) of 1.76 M BBR3 solution in dichloromethane. The resulting mixture was stirred at room temperature for 2 hours, the resultant was poured into 20 ml of a saturated aqueous sodium bicarbonate solution, a solid was precipitated, filtered, washed with water, and dried to obtain a crude product, which was subjected to a silica gel column chromatography eluted with petroleum ether/ethyl acetate (3:2) to obtain a 0.46 g product as a white solid in a yield of 95.8%, mp: 170-172□. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.02 (2H, s, CH2), 6.74˜6.76 (4H, m, 2ArH+NH2), 7.15˜7.40 (7H, m, ArH), 9.49 (1H, s, OH); EI-MS m/e (%): 282.0 (M+, 100), 205.0 (37); HREI-MS Calcd. for C16H14N2OS: 282.0827. found: 282.0824.

Provenance & Evidence