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

HRID 37103

Reaction equation

HRID 37103 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][NH:7][C:6]=2[CH:13]=1.[CH3:14][N:15](C)C=O>C(N)CN.O>[C:14]([C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][NH:7][C:6]=2[CH:13]=1)#[N:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 107526456-Bromo-2,2-dimethyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

Product 1

HCID 105356226-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3301EthylenediamineSolvent

Conditions

Temperature
150 °C

Procedure

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.

Workup

  1. extractionextracted with benzene
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was chromatographed on a silica gel column and elution
  6. washThe crude crystals from the eluate were washed with hexane
  7. customdried

Sources & evidence

ORD record
ord-2811f727f53b47319efad94b5af3cd0c
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Linked notes

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