Diazomethane → 2-Methoxy-7-chloro-5-phenyl-1H-1,5-benzodiazepin-4-one

HRID 261166Notes

Reaction equation

HRID 261166 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7](=[O:18])[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[N+](=[CH2:23])=[N-]>CO.CCOCC>[CH3:23][O:18][C:7]1[NH:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][C:4]=2[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9](=[O:17])[CH:8]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 89657Desmethylclobazam

Product 1

HCID 203952102-Methoxy-7-chloro-5-phenyl-1H-1,5-benzodiazepin-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 11.4 g of 7-chloro-5-phenyl-1H-1,5-benzodiazepine-2,4-dione stirred in 150 ml methanol is added, dropwise, approximately 2.1 g of diazomethane in ether. After addition is complete, the reaction is stirred for 1 hour and filtered. The filtrate is evaporated and the residue diluted with a small amount of ether. The suspension is filtered and the filtrate evaporated to give the title compound.

Workup

  1. additionis added
  2. additionAfter addition
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. additionthe residue diluted with a small amount of ether
  6. filtrationThe suspension is filtered
  7. customthe filtrate evaporated

Sources & evidence

ORD record
ord-2b2af211b945453c9f78dcac91e05885
Source dataset
uspto-grants-1979_08
Patent number
US04164498

Reaction notes

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