Butanedione → 6-cyano-3,4-dihydro-2,2-dimethyl-4-(2,5-dimethyl-3-furyl)-2H-1,4-benzoxazine

HRID 37117

Reaction equation

HRID 37117 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][NH:8][C:7]=2[CH:14]=1)#[N:2].[CH3:15][C:16](=[O:20])[C:17](=O)[CH3:18].[C:21]1(C)C=CC(S(O)(=O)=O)=C[CH:22]=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[CH2:9][N:8]([C:18]3[CH:17]=[C:16]([CH3:15])[O:20][C:21]=3[CH3:22])[C:7]=2[CH:14]=1)#[N:2]

Participants

5

Reactant 3

HCID 650ButanedioneHCID 6101p-Toluenesulfonic acidHCID 105356226-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

Product 1

HCID 199345726-cyano-3,4-dihydro-2,2-dimethyl-4-(2,5-dimethyl-3-furyl)-2H-1,4-benzoxazine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 2 ml of toluene were dissolved 0.5 g of 6-cyano3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine, 1.2 ml of 2,3-butanedione and a catalytic amount of p-toluenesulfonic acid and the mixture was stirred at 100° C. for 2 days. The solvent was then distilled off under reduced pressure and the residue was re-dissolved in toluene, washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was purified by silica gel column chromatography to give 0.15 g of 6-cyano-3,4-dihydro-2,2-dimethyl-4-(2,5-dimethyl-3-furyl)-2H-1,4-benzoxazine.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. dissolutionthe residue was re-dissolved in toluene
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1cb012ca07d148ccb63022c8e5fbaf45
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Linked notes

Loading…