Hydrochloric Acid → 2,3-dichloro-N-(2-{3-[2-(4-cyanophenyl)ethyl]-2-oxoimidazolidin-1-yl}ethyl)-N-methylbenzenesulphonamide

HRID 1591755Notes

Reaction equation

HRID 1591755 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11]([N:14]([CH3:23])[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22])(=[O:13])=[O:12].Br[CH2:25][CH2:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1.Cl>CN(C)C=O.O>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11]([N:14]([CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][N:19]([CH2:25][CH2:26][C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)[C:18]1=[O:22])[CH3:23])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 128865484-(2-Bromoethyl)benzonitrileHCID 586386962,3-Dichloro-N-methyl-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzenesulphonamide

Product 1

HCID 694246682,3-dichloro-N-(2-{3-[2-(4-cyanophenyl)ethyl]-2-oxoimidazolidin-1-yl}ethyl)-N-methylbenzenesulphonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

34 mg (0.84 mmol) of NaH (60%) were added to a solution of 290 mg (0.82 mmol) of 2,3-dichloro-N-methyl-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzenesulphonamide in 10 ml of dimethylformamide, and the mixture was stirred at room temperature for 10 minutes. 177 mg (0.84 mmol) of 4-(2-bromoethyl)benzonitrile were then added. The reaction mixture was stirred at 50° C. overnight. The mixture was then poured into water, 1 N HCl was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulphate and concentrated. The crude product obtained in this manner was purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 0-3%).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. overnight
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb4fa45f4b0445f08f275888c0599d58
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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