Hydrazinecarboxaldehyde → HCID 22599545, compound

HRID 1760108Notes

Reaction equation

HRID 1760108 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. 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 to 96:4 CH2Cl2/MeOH
  6. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-0675fdda4a424a84a718d51dc547f129
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

Loading…