Benzeneacetic acid, hydrazide → HCID 16075309, compound

HRID 1795110Notes

Reaction equation

HRID 1795110 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][NH2:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:22][C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[CH:25]=O)(=[O:21])=[O:20])=[CH:15][CH:14]=1>CCO.C(O)(=O)C>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH2:22][C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2/[CH:25]=[N:11]/[NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:21])=[O:20])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 70301Benzeneacetic acid, hydrazideHCID 11097747HCID 11097747, compound

Product 1

HCID 16075309HCID 16075309, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of-phenylacetic acid hydrazide (0.24 mmol) in absolute EtOH 10 mL and acetic acid 0.4 mL is added 2-{[(4-methylphenyl)sulfonyl]methyl}benzaldehyde (0.22 mmol). The reaction is stirred at room temperate for 2.5 hr with white ppt formation. The reaction mixture is then filtered. The solid is triturated with MeOH to give N′-[(1E)-(2-{[(4-methylphenyl)sulfonyl]methyl}phenyl)methylene]-2-phenylacetohydrazide in 78% yield. 1H NMR (400 MHz, DMSO-d6) □ 11.50–11.25 (2s, 1H), 8.22–8.13 (2s, 1H), 7.79 (m, 1H), 7.56 (m, 2H), 7.31 (m, 10H), 4.93–4.80 (2s, 2H), 3.95–3.57 (2s, 2H), 2.36–2.31 (2s, 3H). ESI− for C23H22N2O3S, m/z 405 (M−H)−.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customThe solid is triturated with MeOH

Sources & evidence

ORD record
ord-dae8af03c7dd41beba51b60bd355b820
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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