Diazepam → Diazepam N-oxide

HRID 1376305ノート

反応式

HRID 1376305 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.ClC1C=C(C=CC=1)C(OO)=[O:26]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N+:8]([O-:26])=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1

参加物

4

反応物 2

HCID 3016DiazepamHCID 70297m-Chloroperbenzoic acid

生成物 1

HCID 72793Diazepam N-oxide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

5.70 g (20 mmol) of 7-chloro-1-methyl-5-phenyl-1H-1,4-benzodiazepine-2(3H)on (manufactured by Sigma, No. T 8275) are dissolved in 150 ml of dichloromethane and 13.8 g (40 mmol) of 3-chloro-peroxybenzoic acid (manufactured by Aldrich, No. 27.303-1) are added under stirring at 20° C. Stirring of the solution is continued for 1.5 h at 20° C. Then the reaction mixture is washed first with 200 ml of 5% NH3 and subsequently with 200 μl of 0.1 n NaOH. The solvent is removed on an rotatione evaporator and the remaining oily residue is dissolved in 25 ml of isopropanol under heating to 40°-45° C. Subsequently, the product is allowed to crystallize under slow cooling down to room temperature. 2 hours after the onset of crystallization, the solid product 2 is drawn off and washed with 50 ml of isopropanol and 50 ml of diisopropylether. The mixture is then dried over night over paraffin in an exsiccator.

後処理

  1. addition27.303-1) are added
  2. stirringStirring of the solution
  3. washThen the reaction mixture is washed first with 200 ml of 5% NH3 and subsequently with 200 μl of 0.1 n NaOH
  4. customThe solvent is removed on an rotatione evaporator
  5. dissolutionthe remaining oily residue is dissolved in 25 ml of isopropanol
  6. temperatureunder heating to 40°-45° C
  7. customto crystallize
  8. temperatureunder slow cooling down to room temperature
  9. custom2 hours after the onset of crystallization
  10. washwashed with 50 ml of isopropanol and 50 ml of diisopropylether
  11. dry with materialThe mixture is then dried over night over paraffin in an exsiccator

出典と根拠

ORDレコード
ord-cdc181c2de9846f393f162142ee3b313
出典データセット
uspto-grants-1997_09
特許番号
US05662911

反応ノート

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