Methyl p-toluenesulfonate → 3,3-Dimethyl-4-hydroxymethyl-2-phenylthiazolidinium p-toluenesulfonate

HRID 2081508Notes

Reaction equation

HRID 2081508 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][S:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]1[CH3:14].[C:15]1([CH3:26])[CH:20]=[CH:19][C:18]([S:21]([O:24]C)(=[O:23])=[O:22])=[CH:17][CH:16]=1>CC(C)=O>[C:15]1([CH3:26])[CH:16]=[CH:17][C:18]([S:21]([O-:24])(=[O:22])=[O:23])=[CH:19][CH:20]=1.[CH3:14][N+:4]1([CH3:15])[CH:3]([CH2:2][OH:1])[CH2:7][S:6][CH:5]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 150522584-Hydroxymethyl-3-methyl-2-phenylthiazolidine

Product 1

HCID 150522593,3-Dimethyl-4-hydroxymethyl-2-phenylthiazolidinium p-toluenesulfonateYield 184.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 10 ml of acetone, 1.00 g of 4-hydroxymethyl-3-methyl-2-phenylthiazolidine and 0.89 g of methyl p-toluenesulfonate were heated under reflux for 52 hours. The mixture was then placed under reduced pressure to distill off the solvent, and ether was added to the residue. Insolubles were washed with ether and dried under reduced pressure to give 1.74 g of the desired compound

Workup

  1. temperatureunder reflux for 52 hours
  2. distillationto distill off the solvent, and ether
  3. additionwas added to the residue
  4. washInsolubles were washed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8bd4224abf5344a4aeaf9d9d0a73c67d
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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