Acetic Acid → N-(2-hydroxyethyl)-N-methylmesitylenesulphonamide mesitylenesulphonate

HRID 1856256Notes

Reaction equation

HRID 1856256 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:14][NH:15][CH2:16][CH2:17][OH:18].C(O)(=O)C>N1C=CC=CC=1>[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([OH:18])(=[O:11])=[O:10].[OH:18][CH2:17][CH2:16][N:15]([CH3:14])[S:9]([C:2]1[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=1[CH3:13])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80162-(Methylamino)ethanolHCID 130462-Mesitylenesulfonyl chloride

Product 1

HCID 23346524N-(2-hydroxyethyl)-N-methylmesitylenesulphonamide mesitylenesulphonateYield 1,622.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

66 g (0.3 mole) mesitylenesulphonyl chloride in 37.5 ml pyridine were added dropwise at -5° C. to 11.2 g (0.015 mole) 2-methylaminoethanol. The reaction mixture was kept in a cooler (4° C.) overnight and then poured on ice. 20 ml acetic acid were added and the product was washed with water, taken up in diethyl ether, washed with water and dried with Na2SO4. The solvent was removed in vacuum, giving 55.7 g pale yellow crystals of the title compound, m.p. 94° C.

Workup

  1. customwas kept in a cooler (4° C.) overnight
  2. additionpoured on ice
  3. washthe product was washed with water
  4. washwashed with water
  5. dry with materialdried with Na2SO4
  6. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-435aab59895f4f4e9f160e7a43157c0b
Source dataset
uspto-grants-1980_08
Patent number
US04218476

Reaction notes

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