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

HRID 851993Notes

Reaction equation

HRID 851993 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]([CH:28]([F:30])[F:29])=[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:27]=[CH:26][C:25]([CH:28]([F:30])[F:29])=[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 27386834-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamideHCID 575899071-(Bromomethyl)-4-(difluoromethyl)benzene

Product 1

HCID 115830704-chloro-N-(4-difluoromethyl-benzyl)-N-(2-oxo-azepan-3-yl)-benzenesulfonamideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamide (0.45 g, 1.50 mmol), 1-bromomethyl-4-difluoromethyl-benzene (0.66 g, 3.00 mmol), potassium carbonate (2.09 g, 15.0 mmol) and potassium iodide (0.05 g, 0.20 mmol) in 15 ml dimethylformamide were stirred at 65° C. for 5 hours. Extraction with water/ethylacetate and chromatography on silicagel with ethylacetate/heptane (90/10 to 1/0) yielded 0.63 g (94%) 4-chloro-N-(4-difluoromethyl-benzyl)-N-(2-oxo-azepan-3-yl)-benzenesulfonamide as white solid, MS: m/e (%)=443.0 (MH+, 100).

Workup

  1. extractionExtraction with water/ethylacetate and chromatography on silicagel with ethylacetate/heptane (90/10 to 1/0)

Sources & evidence

ORD record
ord-96ba3d457c2140679a83886910e6f828
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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