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

HRID 414542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414542
[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

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 542260132,6-Dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-68a83aa754e64e7bbadcb38e49d7e975
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04792557

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