Methyl iodide → HCID 54427130, compound

HRID 1730748Notes

Reaction equation

HRID 1730748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.CI.[C:24](=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:24][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20348745HCID 20348745, compound

Product 1

HCID 54427130HCID 54427130, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 19.9 gm (0.059 mol) of [1-(2'-chloro-4-biphenylyl)-ethylsulfinyl]-acetic acid and 12.5 gm (0.088 mol) of methyl iodide in 120 ml of dry dimethyl sulfoxide was admixed with 12.2 gm (0.088 mol) of dry potassium carbonate, and the mixture was stirred at room temperature for 19 hours. The crude reaction product was precipitated with water and extracted with ethyl acetate (yield: 23.1. gm). For purification, the obtained crude product was purified by chromatography on 1200 gm of silicagel with cyclohexane ethyl acetate = 1/1. The combined fractions with an Rf -value of 0.23 (on carrier 2) were combined and evaporated, leaving 6.2 gm (31.2% of theory) of the title compound; oil, Rf -value: 0.23 on carrier 1 with cyclohexane/ethyl acetate = 1/1.

Workup

  1. customThe crude reaction product
  2. customwas precipitated with water
  3. extractionextracted with ethyl acetate (yield: 23.1. gm)
  4. customFor purification
  5. customthe obtained crude product
  6. customwas purified by chromatography on 1200 gm of silicagel with cyclohexane ethyl acetate = 1/1
  7. customevaporated

Sources & evidence

ORD record
ord-3dd085182d6348d8ac7c26b600441b15
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

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