Acetohydrazide → 1,5-Dimethyl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

HRID 1485477Notes

Reaction equation

HRID 1485477 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7](=S)[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[NH:3]1.[C:14]([NH:17][NH2:18])(=O)[CH3:15]>C(O)CCC>[CH3:15][C:14]1[N:6]2[C:5]3[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=3[NH:3][CH:2]([CH3:1])[CH2:8][C:7]2=[N:18][N:17]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 303360874389-71-2

Product 1

HCID 4000941,5-Dimethyl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepineYield 69.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A disposable tube was charged with 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione (163 mg, 0.848 mmol) and a stirbar. nBuOH (5 mL) was added, followed by acetohydrazide (126 mg, 1.695 mmol), and the solution was stirred at 130° C. overnight. The solution was concentrated and purified by silica gel chromatography (eluting with methylene chloride/methanol/1% ammonium hydroxide) to yield 1,5-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine as an off-white amorphous solid (0.126 g, 0.588 mmol, 69%).

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by silica gel chromatography (eluting with methylene chloride/methanol/1% ammonium hydroxide)

Sources & evidence

ORD record
ord-1fefc1498c1c4bc1aff32781a2577c80
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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