Hydrazinecarboxaldehyde → HCID 22599545, compound

HRID 1267188Notes

Reaction equation

HRID 1267188 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 to 96:4 CH2Cl2/MeOH.

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 to 96:4 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-14dcdb4915704c58b55350937feda0c5
Source dataset
uspto-grants-2003_04
Patent number
US06552013B1

Reaction notes

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