Water → HCID 17911674, compound

HRID 24948Notes

Reaction equation

HRID 24948 reaction equation
[CH3:1]C(C)([O-])C.[K+].CN(C)[CH2:9][CH2:10][S:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)(=[O:13])=[O:12].CI.O>CS(C)=O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([N:14]([CH3:1])[S:11]([CH:10]=[CH2:9])(=[O:13])=[O:12])=[CH:16][CH:17]=1)([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 225695824-(2-Dimethylamino-ethylsulphonylamino)-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 17911674HCID 17911674, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.49 g (4.4 mmol) of potassium tert.butoxide are added at ambient temperature to a solution of 1.1 g (4 mmol) of 4-(2-dimethylamino-ethylsulphonylamino)-nitrobenzene (Example 379a) in 20 ml of DMSO. After 1.5 hours stirring 0.85 g (6 mmol) of methyl iodide are added. The mixture is stirred for 18 hours, then the reaction solution is poured into water and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate and the solvent is eliminated in vacuo. 0.9 g of ethenesulphonic acid-N-(4-nitrophenyl)-N-methyl-amide are obtained as a crude product. 0.75 g of this crude product are dissolved in ethanol and combined with an excess of dimethylamine. After 18 hours stirring the mixture is evaporated to dryness.

Workup

  1. additionare added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulphate

Sources & evidence

ORD record
ord-4b9582b0167c4fd6a613ea57046cb995
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

Loading…