Water → HCID 18005695, compound

HRID 1373122Notes

Reaction equation

HRID 1373122 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].CC(C)([O-])C.[K+].Cl[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25].O>CS(C)=O>[CH3:25][N:24]([CH3:26])[CH2:23][CH2:22][N:5]([C:6]1[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:10][CH:11]=1)[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 843283N-(3-nitrophenyl)methanesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 18005695HCID 18005695, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

5 g (23.1 mmol) of 3-methylsulphonylamino-nitrobenzene are dissolved in 50 ml of DMSO and combined with 6.5 g (58 mmol) of potassium tert. butoxide while cooling with ice. The solution thus obtained is added dropwise to a solution of 5 g (34.7 mmol) of 2-chloro-N,N-dimethyl-ethylamine in 30 ml of DMSO. The mixture is stirred for 2 hours at ambient temperature and then heated for 6 hours to 100° C. After cooling to ambient temperature 400 ml of water are added. The mixture is extracted with ethyl acetate. Water and 1 N hydrochloric acid are added to the combined organic phases until an acid reaction is obtained. The aqueous phase is washed with ethyl acetate. Then the aqueous phase is made alkaline with sodium carbonate and the product is extracted with ethyl acetate. Drying the combined organic phases over magnesium sulphate and eliminating the solvents in vacuo yields the product as a red oil.

Workup

  1. temperaturewhile cooling with ice
  2. customThe solution thus obtained
  3. temperatureheated for 6 hours to 100° C
  4. additionare added
  5. extractionThe mixture is extracted with ethyl acetate
  6. additionWater and 1 N hydrochloric acid are added to the combined organic phases until an acid reaction
  7. customis obtained
  8. washThe aqueous phase is washed with ethyl acetate
  9. extractionthe product is extracted with ethyl acetate
  10. dry with materialDrying the combined organic phases over magnesium sulphate

Sources & evidence

ORD record
ord-fb9e7a6b02d54dbc932918623ff594f6
Source dataset
uspto-grants-2007_01
Patent number
US07160901B2

Reaction notes

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