Triethylamine → Methyl 2-(2-methoxyacetamido)benzoate

HRID 1534853

Reaktionsgleichung

Reaktionsgleichung von HRID 1534853
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(N(CC)CC)C.[CH3:19][O:20][CH2:21][C:22](Cl)=[O:23].[OH-].[Na+]>C(Cl)Cl>[CH3:19][O:20][CH2:21][C:22]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])=[O:23]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 14798Sodium HydroxideHCID 96623Methoxyacetyl chloride

Produkt 1

HCID 836497Methyl 2-(2-methoxyacetamido)benzoateAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3.02 g (20 mmol) of methyl anthranilate in 30 ml of methylene chloride was added 2.22 g (22 mmol) of triethylamine. Into the mixture, a solution of 2.39 g (22 mmol) of methoxyacetyl chloride in 15 ml of methylene chloride was dropwise added under chilling with ice. The resulting mixture was then stirred for 1 hour. After adding ice, the stirred mixture was made alkaline by addition of 1 N aqueous sodium hydroxide and then extracted with chloroform. The organic portion was collected and washed sequentially with 3 N HCl, 6 N HCl, water and saturated aqueous sodium chloride. The washed chloroform portion was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain 3.6 g of the desired compound.

Aufarbeitung

  1. temperatureunder chilling with ice
  2. additionAfter adding ice
  3. extractionextracted with chloroform
  4. customThe organic portion was collected
  5. washwashed sequentially with 3 N HCl, 6 N HCl, water and saturated aqueous sodium chloride
  6. dry with materialThe washed chloroform portion was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1e5a6fa89c62481fb6d6f2ff938ed14f
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05091403

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