Potassium Iodide → 4-chloro-N-(4-cyano-benzyl)-N-(2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 851994Notes

Reaction equation

HRID 851994 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:29]=[CH:28][C:25]([C:26]#[N:27])=[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]([CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 27386834-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamide

Product 1

HCID 184551434-chloro-N-(4-cyano-benzyl)-N-(2-oxo-azepan-3-yl)-benzenesulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamide (1.21 g, 4.00 mmol), 4-(bromomethyl)-benzonitrile (0.79 g, 4.00 mmol), potassium carbonate (5.58 g, 40.0 mmol) and potassium iodide (0.13 g, 0.80 mmol) in 200 ml dimethylformamide were stirred at 65° C. for 16 hours. Extraction with water/ethylacetate and chromatography on silicagel with ethylacetate yielded 1.05 g (63%) 4-chloro-N-(4-cyano-benzyl)-N-(2-oxo-azepan-3-yl)-benzenesulfonamide as white solid, MS: m/e (%)=418.1 (MH+, 100).

Workup

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

Sources & evidence

ORD record
ord-0d574b37941247e19c198a37aff3e2c9
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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