Dimethylformamide → HCID 72359972, compound

HRID 2103855Notes

Reaction equation

HRID 2103855 reaction equation
[OH:1][C:2]1[C:3]([C:18](=O)[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=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>[OH:1][C:2]1[C:3]([C:18](=[N:22][NH:21][C:23]([NH:25][C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)=[S:24])[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 67050335HCID 67050335, compound

Product 1

HCID 72359972HCID 72359972, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

1-[4-Hydroxy-5-(4-isobutylphenyl)-1-methyl-1H-pyrazol-3-yl]ethanone (0.179 mmol, 48.8 mg) and 4-hydrazinocarbonothioylaminobenzoic acid (0.179 mmol, 37.9 mg) were stirred with dimethylformamide (2.5 mL) and three drops of concentrated hydrochloric acid at room temperature for 24.5 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 (62.6 mg, yield 75%).

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-d9a6f81ea17644dd858856ee9de5e40d
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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