Methyl p-toluenesulfonate → HCID 86740528, compound

HRID 637534Notes

Reaction equation

HRID 637534 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7]([O:10]C)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:13][S:14][CH2:15][C:16](=[O:35])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([O:31][C:32](=[O:34])[CH3:33])[CH2:27][O:28][CH2:29][CH3:30])=[CH:20][CH:19]=1>CCOCC>[C:1]1([CH3:12])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[C:32]([O:31][CH:26]([CH2:27][O:28][CH2:29][CH3:30])[CH2:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:16]([CH2:15][S+:14]([CH3:1])[CH3:13])=[O:35])=[CH:23][CH:22]=1)(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 20257098HCID 20257098, compound

Product 1

HCID 86740528HCID 86740528, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 7 g quantity of methyl p-toluenesulfonate was added to 3.41 g of 4-(2-acetoxy-3-ethoxypropoxy)phenylcarbamoylmethyl methyl sulfide. The mixture was stirred at room temperature for 8 hours. Ether was added to the reaction mixture and the insoluble solid was filtered off, and recrystallized from ethanol-ether, giving 5.10 g of 4-(2-acetoxy-3-ethoxypropoxy)phenylcarbamoylmethyldimethylsulfonium p-toluenesulfonate (Compound 2) in 96.6% yield, M.P. 100° to 105° C.

Workup

  1. filtrationthe insoluble solid was filtered off
  2. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-87eca62d0b5944a28a0b6807c85e47b7
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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