Diazepam → Diazepam N-oxide

HRID 1376305Notes

Reaction equation

HRID 1376305 reaction equation
[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

Participants

4

Reactant 2

HCID 3016DiazepamHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 72793Diazepam N-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cdc181c2de9846f393f162142ee3b313
Source dataset
uspto-grants-1997_09
Patent number
US05662911

Reaction notes

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