Methanol → N-(2,4-dimethoxybenzyl)thiazol-2-amine

Participants

Reaction Steps

2,4 Dimethoxybenzaldehyde (25 g, 150 mmol, 1 eq), 2 aminothiazole (15.1 g, 150 mmol, 1 eq) and piperidine (150 mg, 1.76 mmol, 0.012 eq) were combined in dichloroethane (500 ml) and the reaction mixture heated to reflux over sieves for 18 hours. The sieves were removed by filtration and the reaction mixture diluted with MeOH (300 ml). Sodium borohydride (25 g, 662 mmol, 4.4 eq) was added portionwise and the reaction mixture heated to reflux for 2 hours. The mixture was cooled, quenched with water and the organic solvent evaporated in vacuo. The reaction mixture was extracted into ethyl acetate and the combined organic solutions extracted with 2M HCl. The acidic solution was basified with potassium carbonate, re-extracted into ethyl acetate, dried over sodium sulphate, filtered and evaporated in vacuo. The crude material was purified by column chromatography eluting with 9:1 DCM:MeOH to yield the title compound (24 g, 96 mmol, 64%).

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