Acetohydrazide → HCID 70979284, compound

HRID 1485482Notes

Reaction equation

HRID 1485482 reaction equation
[CH3:1][C:2]1([CH3:14])[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:15]([NH:18][NH2:19])(=O)[CH3:16]>C(O)CCC>[CH3:16][C:15]1[N:6]2[C:5]3[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=3[NH:3][C:2]([CH3:14])([CH3:1])[CH2:8][C:7]2=[N:19][N:18]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 86718511HCID 86718511, compound

Product 1

HCID 70979284HCID 70979284, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A disposable tube was charged with 4,4-dimethyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione (600 mg, 2.91 mmol) and a stirbar. nBuOH (30 mL) was added, followed by acetohydrazide (431 mg, 5.82 mmol), and the solution was stirred at 130° C. overnight. The solution was concentrated with celite and purified by silica gel chromatography (eluting with methylene chloride/methanol/ammonium hydroxide) to yield 1,5,5-trimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine as an off-white amorphous solid (0.153 g, 0.67 mmol, 23%).

Workup

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

Sources & evidence

ORD record
ord-3d64576c1dbc445da8f279bb1135d49b
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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