3,5-Dichloroaniline → 3-Bromo-N-(3,5-dichlorophenyl)-1-(phenylsulfonyl)-1H-pyrrole-2-carboxamide

HRID 525007

Reaction equation

HRID 525007 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][N:4]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[C:3]=1[C:16]([O:18]C)=O.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[NH2:24]>>[Br:1][C:2]1[CH:6]=[CH:5][N:4]([S:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)(=[O:8])=[O:9])[C:3]=1[C:16]([NH:24][C:23]1[CH:22]=[C:21]([Cl:20])[CH:27]=[C:26]([Cl:28])[CH:25]=1)=[O:18]

Participants

3

Reactant 2

HCID 122813,5-DichloroanilineHCID 44518095Methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 709813613-Bromo-N-(3,5-dichlorophenyl)-1-(phenylsulfonyl)-1H-pyrrole-2-carboxamideYield 96%

Procedure

Prepared from 2.00 g (5.81 mmol) of methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate and 2.82 g (17.41 mmol) of 3,5-dichloroaniline following the experimental procedure described in Preparation 44a. The product was purified by flash chromatography (0% to 40% hexane/AcOEt) to give 2.64 g (96% yield) of the title compound as a beige solid.

Workup

  1. customThe product was purified by flash chromatography (0% to 40% hexane/AcOEt)

Sources & evidence

ORD record
ord-163acc9cf55841f98c7120bd0d8683c0
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Linked notes

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