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

HRID 1485413Notes

Reaction equation

HRID 1485413 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]>CCCCO>[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 45%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione (200 mg, 1.04 mmol) and acetohydrazide (150 mg, 2.07 mmol) in n-BuOH (10 mL) was heated at 130° C. overnight. The reaction mixture was evaporated, and then water (10 mL) was added, extracted with ethyl acetate (10 mL), dried with Na2SO4, and concentrated to give the crude product, which was purified by prep-TLC to give 1,5-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (100 mg, 45%).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater (10 mL) was added
  3. extractionextracted with ethyl acetate (10 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by prep-TLC

Sources & evidence

ORD record
ord-5c2a6ecb2761459d8a570616bf93ab3e
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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