4-Hydroxybenzoic acid hydrazide → HCID 2316781, compound

HRID 1985017Notes

Reaction equation

HRID 1985017 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][C:13]1[S:17][C:16]([CH:18]=O)=[CH:15][CH:14]=1>C(O)(=O)C.CCO>[CH3:18][C:16]1[S:17][C:13]([CH:12]=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 616635-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 2316781HCID 2316781, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-benzoic acid hydrazide (0.25 g, 0.0016 mol) and 5-methyl-2-thiophenecarboxaldehyde (0.20 g, 0.0016 mol) in abs. EtOH (10 mL), was added 1 drop of acetic acid. The reaction mixture was refluxed for 4 hours. The reaction mixture was cooling to room temperature and concentrated to remove solvent. The resulting residue was solidified by EtOAc to give white solid 0.24 g, in 57% yield, mp: 215.7° C. 1H NMR (CD3OD) δ 8.38 (s, 1H), 7.79 (d, 2H), 7.17 (s, 1H), 6.86 (d, 2H), 6.77 (s, 1H), 2.49 (s, 3H), 1.31. 13C NMR (CDCl3) δ 166.5, 162.8, 145.6, 144.8, 138.1, 132.4, 130.7, 127.1, 124.8, 116.3, 15.6. Anal. Calcd for C13H12N2O2 S: C, 59.98; H, 4.65; N, 10.76. Found: C, 59.98; H, 4.45; N, 10.40.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationconcentrated
  3. customto remove solvent

Sources & evidence

ORD record
ord-ec872d64e83541b7aee310f45c96167a
Source dataset
uspto-grants-2009_06
Patent number
US07544838B2

Reaction notes

Loading…