Dimethylformamide → 4-{[(2-{1-[5-(3,4-dimethylphenyl)-1-methyl-4-hydroxy-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonothioyl]amino}benzoic acid

HRID 1881562Notes

Reaction equation

HRID 1881562 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=O)[CH3:16])[C:10]=2[OH:18])[CH:5]=[CH:6][C:7]=1[CH3:8].[NH:19]([C:21]([NH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=[S:22])[NH2:20].CN(C)C=O>Cl.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=[N:20][NH:19][C:21]([NH:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[S:22])[CH3:16])[C:10]=2[OH:18])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 670500831-[5-(3,4-dimethylphenyl)-1-methyl-4-hydroxy-1H-pyrazol-3-yl]ethanone

Product 1

HCID 723600984-{[(2-{1-[5-(3,4-dimethylphenyl)-1-methyl-4-hydroxy-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonothioyl]amino}benzoic acidYield 68.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

1-[5-(3,4-Dimethylphenyl)-1-methyl-4-hydroxy-1H-pyrazol-3-yl]ethanone (0.2423 mmol, HPLC purity 84.3%, 70.2 mg) and 4-hydrazinocarbonothioylaminobenzoic acid (0.2423 mmol, 51.2 mg) were stirred with dimethylformamide (3 mL) and three drops of concentrated hydrochloric acid at room temperature for 8.5 hours. After addition of water, the precipitated yellow solid was recovered by filtration, washed with water and dried by means of a vacuum pump. The resulting solid was stirred with chloroform/n-hexane for a while, then recovered by filtration and dried by means of a vacuum pump to give the desired product as a pale yellow solid (72.3 mg, yield 68%).

Workup

  1. filtrationthe precipitated yellow solid was recovered by filtration
  2. washwashed with water
  3. customdried by means of a vacuum pump
  4. filtrationrecovered by filtration
  5. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-132dc3c3b2b44f22a3a77d45906ec028
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

Loading…