Methyl iodide → 2,6-dimethoxy-4-(methoxy-carbonyl)-N-methyl-carbanilic acid benzyl ester

HRID 542971Notes

Reaction equation

HRID 542971 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:12]=1[O:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH3:28])[C:11]1[C:12]([O:23][CH3:24])=[CH:13][C:14]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 542260132,6-Dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester

Product 1

HCID 542703972,6-dimethoxy-4-(methoxy-carbonyl)-N-methyl-carbanilic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 34.2 g. of 2,6-dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester and 5.8 g. of sodium hydride (50% dispersion in oil) in 300 ml. of absolute dimethylformamide was stirred at room temperature for 4 hours. The resulting solution was treated with 17 g. of methyl iodide with stirring and ice-cooling. After stirring at room temperature for 1 hour, the dimethylformamide was removed under vacuum at 60° C. Then, 1 liter of water was added to the residue and the emulsion was extracted with two 2 liter portions of ethyl acetate. The organic phases were washed with two 1 liter portions of water, dried over magnesium sulfate and evaporated under vacuum. After recrystallization of the residue from alcohol, there was obtained 2,6-dimethoxy-4-(methoxy-carbonyl)-N-methyl-carbanilic acid benzyl ester having a melting point of 130°-131° C.

Workup

  1. additionA suspension of 34.2 g
  2. additionThe resulting solution was treated with 17 g
  3. temperatureice-cooling
  4. customthe dimethylformamide was removed under vacuum at 60° C
  5. additionThen, 1 liter of water was added to the residue
  6. extractionthe emulsion was extracted with two 2 liter portions of ethyl acetate
  7. washThe organic phases were washed with two 1 liter portions of water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under vacuum
  10. customAfter recrystallization of the residue from alcohol

Sources & evidence

ORD record
ord-4d62140e0f5744de83c86360bcc73cc6
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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