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

HRID 37117

반응식

HRID 37117 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].[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cb012ca07d148ccb63022c8e5fbaf45
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420126

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