对甲苯磺酸 → 6-cyano-3,4-dihydro-2,2-dimethyl-4-(6-oxo-1-cyclohexen-1-yl)-2H-1,4-benzoxazine

HRID 37116

反应方程式

HRID 37116 反应方程式
[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].[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]

参与物

5

反应物 3

HCID 6101对甲苯磺酸HCID 130061,2-环己二酮HCID 105356226-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

产物 1

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

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-543880f311e840e5a659f21d25f74264
来源数据集
uspto-grants-1995_05
专利号
US05420126

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