反応 #74595

反応方程式

2-amino-1,3,4-thiadiazole

2,4-dimethoxy-benzaldehyde

sodium triacetoxyborohydride

→

title compound

収率 45.0%

N-(2,4-Dimethoxybenzyl)-1,3,4-thiadiazol-2-amine

収率 45.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGstirred for 24 hours
2. 2
   その他The reaction was quenched with saturated aqueous sodium bicarbonate solution
3. 3
   抽出extracted with dichloromethane
4. 4
   乾燥The combined organic extracts were dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by flash column chromatography
8. 8
   洗浄eluting with methanol

実験手順

To a solution of 2-amino-1,3,4-thiadiazole (3.05 g, 0.0302 mol) and 2,4-dimethoxy-benzaldehyde (4.55 g, 0.0274 mol) in dichloromethane (125 mL) was added chlorotriisopropoxytitanium (16 mL, 0.067 mol) portionwise over 5 minutes. After stirring for 1 hour, sodium triacetoxyborohydride (11.72 g, 0.05530 mol) was added portion wise and stirred for 24 hours. The reaction was quenched with saturated aqueous sodium bicarbonate solution and adjusted to pH 9 with sodium hydroxide (6 N aqueous solution) and extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with methanol:dichloromethane (gradient 0:1 to 1:9, by volume) to afford the title compound as a white solid, 590 mg, 45% yield.

出典