Iodoethane → N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)carbanilic acid benzyl ester

HRID 462551Notes

Reaction equation

HRID 462551 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+].[CH2:28](I)[CH3:29]>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH2:28][CH3:29])[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 6340IodoethaneHCID 24758Sodium hydrideHCID 542260132,6-Dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester

Product 1

HCID 53836153N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)carbanilic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 103 g. of 2,6-dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester and 17.3 g. of sodium hydride (50% dispersion in oil) in 1 liter of absolute dimethylformamide was stirred at room temperature for 4 hours and subsequently treated with 56.2 g. of ethyl iodide with stirring and ice-cooling. After stirring at room temperature for 30 minutes, the dimethylformamide was removed at 60° C. under vacuum. Then, 1 liter of water was added to the residue and the mixture was extracted with two 1.5 liter portions of ethyl acetate. The ethyl acetate extract was washed with two 700 ml. portions of water, dried over magnesium sulfate and evaporated under vacuum. After recrystallization of the residue from alcohol, there was obtained N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester having a melting point of 85°-86° C.

Workup

  1. additionA suspension of 103 g
  2. additionsubsequently treated with 56.2 g
  3. temperatureice-cooling
  4. customthe dimethylformamide was removed at 60° C. under vacuum
  5. additionThen, 1 liter of water was added to the residue
  6. extractionthe mixture was extracted with two 1.5 liter portions of ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washwas washed with two 700 ml
  9. dry with materialportions of water, dried over magnesium sulfate
  10. customevaporated under vacuum
  11. customAfter recrystallization of the residue from alcohol

Sources & evidence

ORD record
ord-0d840fd243a04e54bcb6c25c1a969570
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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