Dimethylformamide → 1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepine

HRID 2082435Notes

Reaction equation

HRID 2082435 reaction equation
[CH2:1]1[N:12]2[C:13]3[C:3](=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=S)[NH:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[CH2:2]1.O.[NH2:20]N.C[N:23]([CH3:26])C=O>>[CH2:6]1[C:7]2[C:8]3[N:9]([CH:26]=[N:23][N:20]=3)[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[N:12]3[CH:1]=[CH:2][C:3]([C:13]=23)=[CH:4][CH2:5]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 15132539HCID 15132539, compound

Product 1

HCID 678583801,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepineYield 68.2%

Procedure

1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-thione (5 g), hydrazine monohydrate (5 ml) and dimethylformamide (150 ml) were combined and refluxed overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by high performance liquid chromatography (2% methanol/dichloromethane) to yield 3.5 g (68.2%) of product. Recrystallization from tetrahydrofuran gave the analytical sample, mp 177°-178° C.

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by high performance liquid chromatography (2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-910803a65a6a4b8fa29a9ff20f9ae5f0
Source dataset
uspto-grants-1993_02
Patent number
US05189161

Reaction notes

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