Phenol → 2-(4-Hydroxyphenyl)-2,4-dimethyl-2H-1,4-benzothiazin-3(4H)-one

HRID 649315노트

반응식

HRID 649315 반응식
[CH3:1][CH:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1.S(Cl)(Cl)(=O)=O.[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][C:2]1([C:22]2[CH:23]=[CH:24][C:19]([OH:25])=[CH:20][CH:21]=2)[C:7](=[O:8])[N:6]([CH3:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1

참가 물질

6

반응물 4

HCID 996PhenolHCID 24648Sulfuryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 129549032,4-Dimethyl-2H-1,4-benzothiazin-3(4H)-one

생성물 1

HCID 142446972-(4-Hydroxyphenyl)-2,4-dimethyl-2H-1,4-benzothiazin-3(4H)-one수율 90.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzothiazine (4.8 g) in methylene chloride (25 ml), sulfuryl chloride (3.5 g) is added under ice-cooling. The mixture is stirred for 30 minutes, and added into a solution of phenol (2.4 g) and aluminum chloride (3.3 g) in methylene chloride (20 ml) with stirring under ice-cooling. The mixture is stirred for 1 hour under ice-cooling, and washed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The solution is dried over anhydrous sodium sulfate and concentrated in vacuo. A mixture of benzene and n-hexane (1:1) is added to the residue and the separated crystals are collected by filtration to give 6.4 g (90.2%) of the titled compound.

후처리

  1. temperaturecooling
  2. stirringwith stirring under ice-
  3. temperaturecooling
  4. stirringThe mixture is stirred for 1 hour under ice-
  5. temperaturecooling
  6. washwashed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  7. dry with materialThe solution is dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. additionA mixture of benzene and n-hexane (1:1)
  10. additionis added to the residue
  11. filtrationthe separated crystals are collected by filtration

출처 및 근거

ORD 기록
ord-56322e03e8b04735a61756a9ddb7dad4
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04739050

반응 노트

불러오는 중…