Methyl iodide → HCID 21191821, compound

HRID 1421385Notes

Reaction equation

HRID 1421385 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].[C:17]([O-])([O-])=O.[K+].[K+].CI>CN(C)C=O.O>[CH3:17][NH:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[CH2:5][O:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21191823HCID 21191823, compound

Product 1

HCID 21191821HCID 21191821, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 g (23 mmol) of 2-(2'-methylphenoxymethyl)-aniline (Example 1b), 5 g (36 mmol) of K2CO3 and 3.4 g (24 mmol) of methyl iodide in 50 ml of dimethylformamide is stirred overnight at room temperature. The reaction mixture is diluted with water and the aqueous phase is extracted three times with methyl tert-butyl ether. The combined organic phases are extracted with water, dried over MgSO4 and evaporated down. The residue is purified chromatographically using mixtures of hexane and methylene chloride. There is obtained 3.0 g (70% purity, about 40% yield) of the title compound as a yellow oil.

Workup

  1. extractionthe aqueous phase is extracted three times with methyl tert-butyl ether
  2. extractionThe combined organic phases are extracted with water
  3. dry with materialdried over MgSO4
  4. customevaporated down
  5. customThe residue is purified chromatographically using mixtures of hexane and methylene chloride

Sources & evidence

ORD record
ord-39265669b996472e90bbe62fee88450d
Source dataset
uspto-grants-2000_06
Patent number
US06075148

Reaction notes

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