反应详情

To a solution of 2-amino-1,3,4-thiadiazole (3.05 g, 30.2 mmol) and 2,4-dimethoxybenzaldehyde (4.55 g, 27.4 mmol) in dichloromethane (125 mL) was added chlorotriisopropoxytitanium (16 mL, 67.0 mmol) portion-wise 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 aqueous sodium hydroxide (6 N 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 (0-10% methanol in dichloromethane gradient elution) to afford the title compound as a white solid (0.590 g, 86%).

1. stirringstirred for 24 hours
2. customThe reaction was quenched with saturated aqueous sodium bicarbonate solution
3. extractionextracted with dichloromethane
4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel flash column chromatography (0-10% methanol in dichloromethane gradient elution)