Hydrochloric Acid → 4-{[(2-{[5-(3,4-Dichlorophenyl)-4-hydroxy-3-thienyl]methylene}hydrazino)carbonothioyl]amino}benzoic acid

HRID 1881601Notes

Reaction equation

HRID 1881601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([CH:15]=O)[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:17]([C:19]([NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)=[S:20])[NH2:18].CN(C)C=O.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([CH:15]=[N:18][NH:17][C:19]([NH:21][C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=3)=[S:20])[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 848194795-(3,4-Dichlorophenyl)-4-hydroxythiophene-3-carbaldehyde

Product 1

HCID 723600444-{[(2-{[5-(3,4-Dichlorophenyl)-4-hydroxy-3-thienyl]methylene}hydrazino)carbonothioyl]amino}benzoic acidYield 65.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3,4-Dichlorophenyl)-3-hydroxy-4-formylthiophene (52 mg, 0.19 mmol) synthesized in Reference Synthetic Example 26 and 4-hydrazinocarbonothioylaminobenzoic acid (40 mg, 0.19 mmol) were stirred with dimethylformamide (1.9 mL) and concentrated hydrochloric acid (0.1 mL) at room temperature for 14 hours. Water was added to the reaction solution, and the precipitated solid was recovered by filtration and dried. The crude product was stirred with chloroform at room temperature and recovered by filtration to give the desired product as a pale yellow solid (58 mg, yield 65%).

Workup

  1. filtrationthe precipitated solid was recovered by filtration
  2. customdried
  3. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-a75012204d2544a08d2240e6020740f7
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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