Potassium Iodide → 4-chloro-N-(2-oxo-azepan-3-yl)-N-(4-[1,2,4]triazol-1-yl-benzyl)-benzenesulfonamide

HRID 851992Notes

Reaction equation

HRID 851992 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[N:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)=[CH:26][CH:27]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27386834-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamideHCID 27764891-(4-(bromomethyl)phenyl)-1H-1,2,4-triazole

Product 1

HCID 184553954-chloro-N-(2-oxo-azepan-3-yl)-N-(4-[1,2,4]triazol-1-yl-benzyl)-benzenesulfonamideYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamide (0.16 g, 0.52 mmol), 1-[4-(bromomethyl)phenyl]-1H-1,2,4-triazol (0.25 g, 1.03 mmol), potassium carbonate (0.72 g, 5.17 mmol) and potassium iodide (0.02 g, 0.10 mmol) in 5 ml dimethylformamide were stirred at 65° C. for 5 hours. Extraction with water/ethylacetate and chromatography on silicagel with ethylacetate yielded 0.15 g (64%) 4-chloro-N-(2-oxo-azepan-3-yl)-N-(4-[1,2,4]triazol-1-yl-benzyl)-benzenesulfonamide as white solid, MS: m/e (%)=460.1 (MH+, 100).

Workup

  1. extractionExtraction with water/ethylacetate and chromatography on silicagel with ethylacetate

Sources & evidence

ORD record
ord-ba4aa8c69cfc44c6ac5421bf27243573
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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