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

HRID 649315ノート

反応式

HRID 649315 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-56322e03e8b04735a61756a9ddb7dad4
出典データセット
uspto-grants-1988_04
特許番号
US04739050

反応ノート

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