Hydrazinecarboxaldehyde → 5,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

HRID 3566

Reaction equation

HRID 3566 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH2:4][CH2:3][C:2]1=S.[CH:13]([NH:15][NH2:16])=O>C(O)CCC>[CH:13]1[N:1]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[NH:5][CH2:4][CH2:3][C:2]2=[N:16][N:15]=1

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 43814021,3,4,5-tetrahydro-2H-1,5-benzodiazepine-2-thione

Product 1

HCID 218370045,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepineYield 37.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-thione (0.8 g) and 0.80 g of N-formylhydrazine in 8 ml of n-butanol is stirred and refluxed for 18 hours and the solvent removed under vacuum. Ice water is added to the residual solid and the mixture filtered to give 0.312 g of a gray solid, m.p. 162°-165° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. customthe solvent removed under vacuum
  3. additionIce water is added to the residual solid
  4. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-b10c8b2565b240a1a2712a304e908573
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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