Water → HCID 73225133, compound

HRID 2425957Notes

Reaction equation

HRID 2425957 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15]([CH3:17])=O)[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][NH:27][C:28]([C:30]2[S:31][C:32]([C:35]([NH:37][NH2:38])=[O:36])=[CH:33][CH:34]=2)=[O:29])=[CH:20][CH:19]=1.O>CN(C)C=O>[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][NH:27][C:28]([C:30]2[S:31][C:32]([C:35]([NH:37][N:38]=[C:15]([C:12]3[C:13]([OH:14])=[C:9]([C:4]4[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=4)[S:10][CH:11]=3)[CH3:17])=[O:36])=[CH:33][CH:34]=2)=[O:29])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiopheneHCID 57688182HCID 57688182, compound

Product 1

HCID 73225133HCID 73225133, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3,4-Dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (42 mg, 0.14 mmol) and 5-hydrazinocarbonylthiophene-2-carboxylic acid 3-(pyridin-4-yl)propylamide (40 mg, 0.13 mmol) prepared in Reference Synthetic Example 26 were dissolved in N,N-dimethylformamide (1.0 mL) and left at 70° C. for 16 hours and then at room temperature for 24 hours. Water (0.36 mL) was added with stirring, and the precipitated solid was recovered by filtration to give the desired product, 5-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic acid 3-(pyridin-4-yl)propylamide (yield 95%).

Workup

  1. waitat room temperature for 24 hours
  2. filtrationthe precipitated solid was recovered by filtration

Sources & evidence

ORD record
ord-3a2ec59e79e84ab2a200f615aeebde65
Source dataset
uspto-grants-2011_06
Patent number
US07968542B2

Reaction notes

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