Diazomethane → 2-Methoxy-7-chloro-5-phenyl-3H-1,5-benzodiazepin-4-one

HRID 2057918Notes

Reaction equation

HRID 2057918 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[CH2:8][C:9](=[O:17])[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]2[CH:3]=[C:2]([Cl:1])[CH:20]=[CH:19][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 89657Desmethylclobazam

Product 1

HCID 203293162-Methoxy-7-chloro-5-phenyl-3H-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-cc8b749ebe604ec7a218dbd9e696a0d9
Source dataset
uspto-grants-1980_07
Patent number
US04213982

Reaction notes

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