p-Toluenesulfonic acid → 6-cyano-3,4-dihydro-2,2-dimethyl-4-(6-oxo-1-cyclohexen-1-yl)-2H-1,4-benzoxazine

HRID 37116

반응식

HRID 37116 반응식
[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].[C:15]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21].C1(C)C=CC(S(O)(=O)=O)=CC=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:15]3[C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH:20]=3)[C:7]=2[CH:14]=1)#[N:2]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 130061,2-CyclohexanedioneHCID 105356226-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

생성물 1

HCID 104931656-cyano-3,4-dihydro-2,2-dimethyl-4-(6-oxo-1-cyclohexen-1-yl)-2H-1,4-benzoxazine수율 66.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

In 15 ml of toluene were dissolved 0.5 g of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine, 0.33 g of cyclohexane-1,2-dione and a catalytic amount of p-toluenesulfonic acid and using a Dean-Stark trap, the solution was refluxed under heating for 4 hours. After cooling, the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and the resulting crude crystals were washed with ethanol to give 0.5 g of 6-cyano-3,4-dihydro-2,2-dimethyl-4-(6-oxo-1-cyclohexen-1-yl)-2H-1,4-benzoxazine.

후처리

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 4 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washthe resulting crude crystals were washed with ethanol

출처 및 근거

ORD 기록
ord-543880f311e840e5a659f21d25f74264
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420126

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