反応 #1726702

反応方程式

3-Chloro-4-phenyl-1,2,5-thiadiazole

lithium bis(trimethylsilyl)amide

hydrochloric acid

→

3-amino-4-phenyl-1,2,5-thiadiazole

収率 68.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   抽出extracted three times into ether (total 300 ml)
2. 2
   洗浄The combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
3. 3
   乾燥dried over magnesium sulfate
4. 4
   濃縮concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in methanol (50 ml)
6. 6
   温度triethylamine (0.5 ml) was heated
7. 7
   温度to reflux for 15 hr
8. 8
   濃縮again concentrated in vacuo

実験手順

3-Chloro-4-phenyl-1,2,5-thiadiazole (3.19 g, 16.2 mmol) in THF (32 ml) at 0° C. was treated dropwise with a solution of lithium bis(trimethylsilyl)amide in THF (17.0 ml, 1.0 M, 17.0 mmol). After 10 min the mixture allowed to warm to ambient temperature for 1.5 hr, treated with 1N hydrochloric acid, and extracted three times into ether (total 300 ml). The combined organic phases were washed with saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in methanol (50 ml) and triethylamine (0.5 ml) was heated to reflux for 15 hr and again concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 3-amino-4-phenyl-1,2,5-thiadiazole (1.96 g, 68%) as a colorless solid.

出典