2-Chloroethanol → N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide

HRID 1954664Notes

Reaction equation

HRID 1954664 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.Cl[CH2:13][CH2:14][OH:15].[C:16](=[O:19])([O-])[O-].[K+].[K+].[CH3:22]N(C)C=O>>[OH:15][CH2:14][CH2:13][N:10]([CH2:22][CH2:16][OH:19])[S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:11])=[CH:6][CH:5]=1)(=[O:8])=[O:9]

Participants

5

Reactant 4

HCID 342-ChloroethanolHCID 6228DimethylformamideHCID 6269P-ToluenesulfonamideHCID 11430Potassium Carbonate

Product 1

HCID 81565N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamideYield 81%

Conditions

Temperature
110 °C

Procedure

6.84 g (40 mmol) 4-toluenesulfonamide A5, 7 ml (8.37 g, 104 mmol) 2-chloroethanol and 27.64 g (200 mmol) potassium carbonate were suspended in 100 ml dimethylformamide and stirred for 3 days at 110° C. Upon cooling, the reaction mixture was filtrated and the precipitate washed with chloroform. The filtrate was concentrated, the oily residue taken up in chloroform and finally washed with a 10% sodium hydroxide solution. On concentrating the organic solution, 8.4 g of pure product were obtained as light yellow crystals; yield: 81%.

Workup

  1. temperatureUpon cooling
  2. filtrationthe reaction mixture was filtrated
  3. washthe precipitate washed with chloroform
  4. concentrationThe filtrate was concentrated
  5. washfinally washed with a 10% sodium hydroxide solution
  6. concentrationOn concentrating the organic solution

Sources & evidence

ORD record
ord-e549374492934c268c26c7ad08436c97
Source dataset
uspto-grants-2000_09
Patent number
US06124135

Reaction notes

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