5-Chloro-2-methylaniline → N-(5-Chloro-2-methylphenyl)acetamide

HRID 2211905

Reaktionsgleichung

Reaktionsgleichung von HRID 2211905
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([NH2:8])[CH:7]=1.C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C1COCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([NH:8][C:17](=[O:19])[CH3:18])[CH:7]=1

Komponenten

7

Edukt 3

HCID 72605-Chloro-2-methylanilineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Produkt 1

HCID 80000N-(5-Chloro-2-methylphenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5-Chloro-2-methyl-phenylamine (50 g, 353.11 mmol) was dissolved in dry THF (500 mL) followed by addition of triethylamine (61.53 mL, 441.39 mmol) and the whole heated to 60° C. To the stirring solution at 60° C. was added dropwise a solution of acetic anhydride (50 ml, 529.66 mmol) in dry THF (100 mL) and the reaction was stirred at 60° C. overnight. Upon cooling, the reaction was diluted with H2O (500 mL), ethyl acetate (250 mL) and the layers separated. The organics were washed with H2O (250 mL), 1N HCl (250 mL), sat Na2CO3 (250 mL), brine (250 mL), dried (MgSO4) and concentrated to a solid (59.67 g, 324.97 mmol).

Aufarbeitung

  1. temperatureUpon cooling
  2. customthe layers separated
  3. washThe organics were washed with H2O (250 mL), 1N HCl (250 mL)
  4. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-a8ed8df5827746f9acc16b6f99be2e3e
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101886B2

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