反应 #65381

反应方程式

6-bromo-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

N,N-dimethylformamide

→

6-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

溶剂

ethylenediamine

water

反应条件

后处理

1. 1
   萃取extracted with benzene
2. 2
   洗涤The organic layer was washed with water
3. 3
   干燥dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   其他The residue was chromatographed on a silica gel column and elution
6. 6
   洗涤The crude crystals from the eluate were washed with hexane
7. 7
   其他dried

实验过程

A mixture of 480 mg of 6-bromo-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine, 206 mg of cuprous cyanide and 5 ml of N,N-dimethylformamide was stirred at 130° C. for 4 hours and further at 150° C. for 5 hours. This reaction mixture was diluted with 0.5 ml of ethylenediamine and 10 ml of water and extracted with benzene. The organic layer was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was chromatographed on a silica gel column and elution was carried out with ethyl acetate-hexane (10:1). The crude crystals from the eluate were washed with hexane and dried to give 160 mg of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine. This compound has the following physicochemical properties.

来源