Реакция #1726702

Уравнение реакции

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

lithium bis(trimethylsilyl)amide

hydrochloric acid

→

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

Выход 68.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted three times into ether (total 300 ml)
2. 2
   ПромывкаThe combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
3. 3
   Сушкаdried over magnesium sulfate
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in methanol (50 ml)
6. 6
   Температураtriethylamine (0.5 ml) was heated
7. 7
   Температураto reflux for 15 hr
8. 8
   Концентрированиеagain concentrated in vacuo

Методика

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.

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