2-Methoxyaniline → 4-Chloromethyl-N-(2-methoxyphenyl)benzamide

HRID 2418

Reaktionsgleichung

Reaktionsgleichung von HRID 2418
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[Cl:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[O:19])=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 70002-MethoxyanilineHCID 14798Sodium HydroxideHCID 701364-(Chloromethyl)benzoyl chloride

Produkt 1

HCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamideAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

o-Anisidine (0.69 ml, 6.0 mmol) was dissolved in methylene chloride (10 ml) and, with cooling in an ice bath, mixed with 20% sodium hydroxide (5 ml) and 4-chloromethylbenzoyl chloride (1.17 g, 6.0 mmol). After 30 minutes of stirring at the same temperature, the reaction mixture was extracted with methylene chloride and then washed with 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting light beige solid was purified by recrystallization (ether-hexane) to obtain 1.56 g (94.2%) of the title compound in the form of colorless needle crystals.

Aufarbeitung

  1. temperaturewith cooling in an ice bath
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washwashed with 1N hydrochloric acid, water and saturated brine in that order
  4. dry with materialAfter drying on anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customthe resulting light beige solid was purified by recrystallization (ether-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-77cb8f49e98843759fa1c7777b2640d4
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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