Diethyl Ether → HCID 20257091, compound

HRID 637535Notes

Reaction equation

HRID 637535 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5](=[O:19])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])=[CH:9][CH:8]=1.C[I:21].[CH3:22]COCC>CN(C)C=O>[I-:21].[OH:18][CH:15]([CH2:16][OH:17])[CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:5]([CH2:4][CH2:3][S+:2]([CH3:22])[CH3:1])=[O:19])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 10613144HCID 10613144, compound

Product 1

HCID 20257091HCID 20257091, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved in 5 ml of dimethylformamide was 2.85 g of 2-{4-(2,3-dihydroxypropoxy)phenylcarbamoyl}ethyl methyl sulfide. To the solution was added 5.00 g of methyl iodide and the mixture was stirred at room temperature for 12 hours. Ether was added to the reaction mixture and the insoluble solid was filtered off, and recrystallized from methanol-ether, giving 4.05 g of 2-{4-(2,3-dihydroxypropoxy)phenylcarbamoyl}ethyldimethylsulfonium iodide (Compound 3) in 94.8% yield, M.P. 113° to 115° C.

Workup

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

Sources & evidence

ORD record
ord-343229381b0e4717b7862d0848ca36e4
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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