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

HRID 37117

反応式

HRID 37117 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1cb012ca07d148ccb63022c8e5fbaf45
出典データセット
uspto-grants-1995_05
特許番号
US05420126

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