Реакция #1144

Уравнение реакции

2-(2-cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran

sodium azide

ammonium chloride

N,N-dimethylformamide

→

5-[2-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]ethyl ]-1H-tetrazole

Выход 78.1%

Растворители

water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate
2. 2
   ПромывкаAfter the ethyl acetate layer was washed with water
3. 3
   Сушкаdried (MgSO4)
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   ПромывкаFrom the fraction eluted with methanol-chloroform (5:95

Методика

A mixture of 2-(2-cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran (1.20 g), sodium azide (1.09 g), ammonium chloride (0.90 g) and N,N-dimethylformamide (30 ml) was stirred at 130° to 140° C. for 16 hours. The reaction mixture was poured over water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; the residue was subjected to silica gel column chromatography. From the fraction eluted with methanol-chloroform (5:95, v/v), 5-[2-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]ethyl ]-1H-tetrazole (1.05 g, 78%) was obtained, which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 177° to 178° C.

Источник