2-Methoxy-5-acetylaniline → N-(5-acetyl-2-methoxyphenyl)-3-chloro-2-methylpropanamide

HRID 1679338

Reaktionsgleichung

Reaktionsgleichung von HRID 1679338
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:4]=1[NH2:5].[Cl:13][CH2:14][CH:15]([CH3:19])[C:16](Cl)=[O:17]>C1C=CC=CC=1.O>[Cl:13][CH2:14][CH:15]([CH3:19])[C:16]([NH:5][C:4]1[CH:6]=[C:7]([C:10](=[O:12])[CH3:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:17]

Komponenten

5

Edukt 2

HCID 2332832-Methoxy-5-acetylanilineHCID 124174873-Chloro-2-methylpropanoyl chloride

Produkt 1

HCID 53827039N-(5-acetyl-2-methoxyphenyl)-3-chloro-2-methylpropanamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

24.8 g of 2-methoxy 5-acetyl aniline [obtained according to Oelschager Arzneimit. Forschung 8 532-539 (1958)] dissolved in 150 ml benzene are added with 10.6 g of 3-chloro isobutyric acid chloride in 40 ml benzene. The mixture is kept at room temperature for 2 hours under stirring then diluted with 250 ml water. The benzenic phase is separated. The aqueous phase is extracted twice with benzene. The benzenic solutions are united, washed with 2N hydrochloric acid and then with water, dried on sodium sulphate, filtered and evaporated to dryness. The residue is recrystallised from isopropyl ether from which 15.5 g of pure compound are recovered (yield = 77%) -1-(β-chloroα-methyl propionylamino) 2-methoxy 5-acetylbenzene melts at 92°-97°.

Aufarbeitung

  1. customThe benzenic phase is separated
  2. extractionThe aqueous phase is extracted twice with benzene
  3. washwashed with 2N hydrochloric acid
  4. dry with materialwith water, dried on sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue is recrystallised from isopropyl ether from which 15.5 g of pure compound
  8. customare recovered (yield = 77%) -1-(β-chloroα-methyl propionylamino) 2-methoxy 5-acetylbenzene melts at 92°-97°

Quellen und Nachweise

ORD-Eintrag
ord-01415597243c43a491bdfdf49276a943
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04080452

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