1,3,4-Thiadiazol-2-amine → N-(2,4-dimethoxybenzyl)-1,3,4-thiadiazol-2-amine

Participants

Reaction Steps

To a solution of 2-amino-1,3,4-thiadiazole (3.05 g, 30.2 mmol) and 2,4-dimethoxy-benzaldehyde (4.55 g, 27.4 mmol) in dichloromethane (125 mL) was added chlorotriisopropoxytitanium (16 mL, 67 mmol) portionwise over 5 minutes. After stirring for 1 hour, sodium triacetoxyborohydride (11.72 g, 55.3 mmol) was added portion wise and stirred for 24 hours. The reaction was quenched with saturated aqueous sodium bicarbonate solution, adjusted to pH 9 with sodium hydroxide (6 N aqueous solution) and extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (0% to 10% methanol in dichloromethane gradient elution) to afford the title compound as a white solid (590 mg).

Provenance & Evidence