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

HRID 703430Notes

Reaction equation

HRID 703430 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-ff2b865f3e2f463a9ea1d03a9b2ec8d0
Source dataset
uspto-grants-1991_01
Patent number
US04983601

Reaction notes

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