4-Hydroxybenzoic acid hydrazide → HCID 789061, compound

HRID 1667560Notes

Reaction equation

HRID 1667560 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.[N+:12]([C:15]1[S:19][C:18]([CH:20]=O)=[CH:17][CH:16]=1)([O-:14])=[O:13]>C(O)(=O)C.CCO>[N+:12]([C:15]1[S:19][C:18]([CH:20]=[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:17][CH:16]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 782815-Nitrothiophene-2-carboxaldehyde

Product 1

HCID 789061HCID 789061, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-benzoic acid hydrazide (0.3 g, 0.002 mol) and 5-nitro-2-thiophenecarboxaldehyde (0.28 g, 0.002 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 0.55 g, in 95% yield, mp: 194.5° C. 1H NMR (DMSO-d6) δ 11.99 (s, 1H), 10.18 (s, 1H), 8.63 (s, 1H), 8.11 (d, 2H), 7.78 (d, 2H), 7.53 (d, 1H), 6.86 (d, 2H). 13C NMR (DMSO-d6) δ 164.9, 162.9, 152.5, 149.0, 142.0, 132.4, 131.8, 131.1, 125.1, 117.0. Anal. Calcd for C12H9N3O4S: C, 49.48; H, 3.11; N, 14.43. Found: C, 49.55; H, 3.09; N, 14.36.

Workup

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

Sources & evidence

ORD record
ord-ae66e8cd3ec3484792b05a05de049102
Source dataset
uspto-grants-2011_10
Patent number
US08044241B2

Reaction notes

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