Acetohydrazide → 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

HRID 1485375Notes

Reaction equation

HRID 1485375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=S)[NH:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1.[C:21]([NH:24][NH2:25])(=O)[CH3:22]>C(O)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12]3=[N:25][N:24]=[C:21]([CH3:22])[N:11]3[C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 867184911-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one

Product 1

HCID 709795286-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-oneYield 40.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 1-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (1.0 g, 3.3 mmol) and acetohydrazide (1.23 g, 16.6 mmol) in n-butanol (20 ml) was refluxed for 24 h under N2 atmosphere. The solvent was evaporated in vacuo and partitioned between DCM (100 mL) and water (50 mL). The organic phase was dried over Na2SO4 and the solvent was evaporated in vacuo to afford a residue. The residue was purified by column chromatography (silica-gel, DCM:MEOH=30:1) to give 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (430.0 mg, 40%). LRMS (M+H+) m/z: calcd 324.08. found 324. 1H NMR (300 MHz, CD3OD): δ 2.72 (s, 3H), 3.94 (q, J=14.1 Hz, 2H), 7.15-7.24 (m, 3H), 7.40-7.52 (m, 4H), 7.70-7.73 (m, 1H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. custompartitioned between DCM (100 mL) and water (50 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was evaporated in vacuo
  5. customto afford a residue
  6. customThe residue was purified by column chromatography (silica-gel, DCM:MEOH=30:1)

Sources & evidence

ORD record
ord-ec9d33ff21eb4d0895cb1a342376606d
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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