Dimethyl Sulfate → 2,3-Dichloro-N-methyl-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzenesulphonamide

HRID 1591754Notes

Reaction equation

HRID 1591754 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20])(=[O:11])=[O:10].[C:21](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH3:21])[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20])(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 586387222,3-Dichloro-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzenesulphonamide

Product 1

HCID 586386962,3-Dichloro-N-methyl-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzenesulphonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.57 g (1.69 mmol) of 2,3-dichloro-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzenesulphonamide and 0.23 g (1.7 mmol) of potassium carbonate in 10 ml dimethylformamide was stirred at room temperature for 10 minutes, 0.16 ml (1.69 mmol) of dimethyl sulphate were then added and the mixture was stirred at room temperature overnight. The mixture was then diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulphate and concentrated. The product obtained in this manner was crystallized using diethyl ether.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over sodium sulphate
  3. concentrationconcentrated
  4. customThe product obtained in this manner
  5. customwas crystallized

Sources & evidence

ORD record
ord-dd124d3ef1f74defa081155b5a2dc51a
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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