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

HRID 2103832Notes

Reaction equation

HRID 2103832 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=O)[CH3:16])[C:10]=2[OH:18])=[CH:5][CH:4]=1.[NH:21]([C:23]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)=[S:24])[NH2:22].CN(C)C=O>Cl.O>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=[N:22][NH:21][C:23]([NH:25][C:26]3[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=3)=[S:24])[CH3:16])[C:10]=2[OH:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

Product 1

HCID 723601104-{[(2-{1-[5-(4-trifluoromethylphenyl)-1-methyl-4-hydroxy-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonothioyl]amino}benzoic acidYield 89.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

1-[5-(4-trifluoromethylphenyl)-1-methyl-4-hydroxy-1H-pyrazol-3-yl]ethanone (0.1694 mmol, HPLC purity 80%, 60.2 mg) and 4-hydrazinocarbonothioylaminobenzoic acid (0.1694 mmol, 35.8 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. Chloroform/n-hexane was added to the resulting solid, and the precipitated solid was recovered by filtration and dried by means of a vacuum pump to give the desired product as a pale yellow solid (72.2 mg, yield 89%).

Workup

  1. filtrationthe precipitated yellow solid was recovered by filtration
  2. washwashed with water
  3. customdried by means of a vacuum pump
  4. additionChloroform/n-hexane was added to the resulting solid
  5. filtrationthe precipitated solid was recovered by filtration
  6. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-2e5e086253914067bb0a4f78b10a07f1
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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