Hydrazinecarboxaldehyde → HCID 22599545, compound

HRID 1859834Notes

Reaction equation

HRID 1859834 reaction equation
C(S[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH3:15])[C:7](=[O:16])[CH2:6][N:5]=1)C.[CH:17]([NH:19][NH2:20])=O>C(O)CCC>[CH3:15][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:4]2=[N:20][N:19]=[CH:17][N:5]2[CH2:6][C:7]1=[O:16]

Participants

4

Reactant 2

HCID 12229Hydrazinecarboxaldehyde2×HCID 22599567HCID 22599567, compound

Product 1

HCID 22599545HCID 22599545, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1,3-dihydro-5-(ethylthio)-1-methyl-2H-1,4-benzodiazepin-2-one (1 eq.) and formic hydrazide (5.8 eq. Aldrich) in n-butanol (0.1 M in benzodiazepine) was stirred at reflux under N2 for 24 hours. An additional 1.67 eq. of formic hydrazide was added and refluxing continued an additional 16 hours. The yellow solution was evaporated in vacuo and the residue was purified via flash chromatography eluting with a gradient from 98:2® 96:4 CH2Cl2/MeOH. The product was obtained as a white solid.

Workup

  1. temperatureat reflux under N2 for 24 hours
  2. temperaturerefluxing
  3. customThe yellow solution was evaporated in vacuo
  4. customthe residue was purified via flash chromatography
  5. washeluting with a gradient from 98:2® 96:4 CH2Cl2/MeOH
  6. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-181679ad456a40e8b88145d0785413cf
Source dataset
uspto-grants-2003_03
Patent number
US06528505B1

Reaction notes

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