تفاعل #65381

معادلة التفاعل

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

المذيبات

ethylenediamine

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with benzene
2. 2
   غسيلThe organic layer was washed with water
3. 3
   تجفيفdried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   أخرىThe residue was chromatographed on a silica gel column and elution
6. 6
   غسيلThe crude crystals from the eluate were washed with hexane
7. 7
   أخرىdried

الإجراء التجريبي

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.

المصدر