4-Toluenesulfonyl chloride → p-Toluenesulfonamide, N-(2-hydroxyethyl)-N-methyl-, p-toluenesulfonate

HRID 1714826Notes

Reaction equation

HRID 1714826 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][NH:13][CH2:14][CH2:15][OH:16].C(N([CH2:22][CH3:23])CC)C>ClCCl.COC(C)(C)C>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:16][CH2:15][CH2:14][N:13]([CH3:12])[S:7]([C:4]2[CH:5]=[CH:6][C:22]([CH3:23])=[CH:2][CH:3]=2)(=[O:9])=[O:8])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 80162-(Methylamino)ethanolHCID 8471Triethylamine

Product 1

HCID 101216p-Toluenesulfonamide, N-(2-hydroxyethyl)-N-methyl-, p-toluenesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

10.55 g of p-toluenesulphonyl chloride are added to a solution of 2.13 ml of 2-(methylamino)-ethanol and 8 ml of triethylamine in 25 ml of dichloromethane while cooling in ice, and the mixture is stirred at room temperature for 20 hours. The reaction mixture is diluted with 100 ml of tert-butyl methyl ether and washed with 0.1M HCl (50 ml), water (50 ml) and brine (50 ml). The organic phase is dried with sodium sulphate and evaporated, whereupon the title compound crystallizes as white solid. Rt=4.67.

Workup

  1. temperaturewhile cooling in ice
  2. washwashed with 0.1M HCl (50 ml), water (50 ml) and brine (50 ml)
  3. dry with materialThe organic phase is dried with sodium sulphate
  4. customevaporated, whereupon the title compound
  5. customcrystallizes as white solid

Sources & evidence

ORD record
ord-d3755e0389124001af3ab7cdc573d818
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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