Diethyl Ether → 4-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyldimethylsulfonium p-toluenesulfonate

HRID 637533Notes

Reaction equation

HRID 637533 reaction equation
[CH3:1][S:2][CH2:3][C:4](=[O:20])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[CH2:15][O:16][CH2:17][CH3:18])=[CH:8][CH:7]=1.[C:21]1([CH3:32])[CH:26]=[CH:25][C:24]([S:27]([O:30]C)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[CH3:33]COCC>C(Cl)Cl>[C:21]1([CH3:32])[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[CH2:17]([O:16][CH2:15][CH:14]([OH:19])[CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([NH:5][C:4]([CH2:3][S+:2]([CH3:33])[CH3:1])=[O:20])=[CH:11][CH:10]=1)[CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6645Methyl p-toluenesulfonateHCID 133860734-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfide

Product 1

HCID 867405264-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyldimethylsulfonium p-toluenesulfonateYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved in 20 ml of methylene chloride was 2.99 g of 4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfide. To the solution was added 5.50 g of methyl p-toluenesulfonate. The mixture was stirred at room temperature for 24 hours and ether was added to the reaction mixture. The insoluble solid was filtered off and recrystallized from methylene chloride-ether, giving 4.75 g of 4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyldimethylsulfonium p-toluenesulfonate (Compound 1) in 97.7% yield, M.P. 139° to 141° C.

Workup

  1. filtrationThe insoluble solid was filtered off
  2. customrecrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-543c40113e2f4ff5a31afc40436005c6
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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