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

HRID 1881586Notes

Reaction equation

HRID 1881586 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]=[C:6]([CH3:8])[CH:7]=1.[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]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 67050216HCID 67050216, compound

Product 1

HCID 723599714-{[(2-{1-[5-(3,5-dimethylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonothioyl]amino}benzoic acidYield 65%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

1-[5-(3,5-Dimethylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (0.122 mmol, 29.9 mg) and 4-hydrazinocarbonothioylaminobenzoic acid (0.122 mmol, 25.9 mg) were stirred with dimethylformamide (2 mL) and two drops of concentrated hydrochloric acid at room temperature for 24 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 (34.7 mg, yield 65%).

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-c37a5bd3ff564e63b57df7ca41c911f5
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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