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

HRID 1881560Notes

Reaction equation

HRID 1881560 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[C:13]([C:23](=O)[CH3:24])[C:12]=2[OH:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:27]([C:29]([NH:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=1)=[S:30])[NH2:28].CN(C)C=O>Cl.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:14]=[C:13]([C:23](=[N:28][NH:27][C:29]([NH:31][C:32]3[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=3)=[S:30])[CH3:24])[C:12]=2[OH:26])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 670500891-[5-(4-tert-butylphenyl)-1-benzyl-4-hydroxy-1H-pyrazol-3-yl]ethanone

Product 1

HCID 723599354-{[(2-{1-[5-(4-tert-butylphenyl)-1-benzyl-4-hydroxy-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonothioyl]amino}benzoic acidYield 70.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

1-[5-(4-tert-Butylphenyl)-1-benzyl-4-hydroxy-1H-pyrazol-3-yl]ethanone (0.218 mmol, 76 mg) and 4-hydrazinocarbonothioylaminobenzoic acid (0.218 mmol, 46 mg) were stirred with dimethylformamide (3.5 mL) and three drops of concentrated hydrochloric acid at room temperature for 22 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 (83 mg, yield 70%).

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-0053b9127bb142be9f3cb95b383aa75c
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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