4-Chlorobutyryl chloride → [4-(4-Chloro-1-oxobutyl)]-N-methoxy-N-methyl benzeneacetamide

HRID 48015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48015
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH3:12][O:13][N:14]([CH3:24])[C:15](=[O:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C:15]([N:14]([O:13][CH3:12])[CH3:24])=[O:23])=[CH:22][CH:21]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10419762N-Methoxy-N-methyl-2-phenylacetamide

Produkt 1

HCID 9857023[4-(4-Chloro-1-oxobutyl)]-N-methoxy-N-methyl benzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Cool a slurry of aluminum chloride (87 g, 650 mmol) in methylene chloride (100 mL) with an ice bath. Add 4-chlorobutyryl chloride (51 g, 360 mL) dropwise over 0.5 hours. Add N-methoxy-N-methyl-benzeneacetamide (53 g; 300 mmol) over 0.5 hours. Allow the resultant solution to warm to room temperature. Then heat at reflux for 6 hours. Cool the solution to room temperature. Pour the solution into ice (1 L) and add methylene chloride (1 L). Separate the organic phase. Extract the aqueous phase with methylene chloride (2×500 mL). Dry the combined organics over anhydrous magnesium sulfate and concentrate to provide a solid which contains a ca. 1:1 mixture of the title compound and the meta isomer.

Aufarbeitung

  1. temperatureThen heat
  2. temperatureat reflux for 6 hours
  3. customSeparate the organic phase
  4. extractionExtract the aqueous phase with methylene chloride (2×500 mL)
  5. dry with materialDry the combined organics over anhydrous magnesium sulfate
  6. concentrationconcentrate
  7. customto provide a solid which

Quellen und Nachweise

ORD-Eintrag
ord-746321b5ab7a4de6bedeafbd7779cd02
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06700012B2

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