2-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiophene → HCID 73300007, compound

HRID 1094929Notes

Reaction equation

HRID 1094929 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([CH2:23][CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([C:33]([NH:35][NH2:36])=[O:34])=[CH:31][CH:32]=2)=[O:27])[CH2:22][CH2:21][CH2:20][CH2:19]1>CS(C)=O>[N:18]1([CH2:23][CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([C:33]([NH:35][N:36]=[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:34])=[CH:31][CH:32]=2)=[O:27])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiopheneHCID 60206781HCID 60206781, compound

Product 1

HCID 73300007HCID 73300007, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(3,4-Dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (22 mg, 0.075 mmol) in dimethyl sulfoxide (2.0 mL) was heated with 5-(hydrazinocarbonyl)thiophene-2-carboxylic acid [2-(pyrrolidin-1-yl)ethyl]-amide (21 mg, 0.075 mmol) prepared in Reference Synthetic Example 1 at 100° C. for 24 hours. Evaporation of the solvent followed by recrystallization from chloroform (1 mL)-diethyl ether (2 mL) affored 12 mg of the desired product (yield 29%).

Workup

  1. customprepared in Reference Synthetic Example 1 at 100° C. for 24 hours
  2. customEvaporation of the solvent
  3. customfollowed by recrystallization from chloroform (1 mL)-diethyl ether (2 mL)

Sources & evidence

ORD record
ord-9fb8d9a12924486d9bdc3119ef6f177e
Source dataset
uspto-grants-2012_03
Patent number
US08134013B2

Reaction notes

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