Chloroacetyl chloride → N-(4-chlorophenacyl) chloroacetamide

HRID 866850

Reaktionsgleichung

Reaktionsgleichung von HRID 866850
Cl.[Cl:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][NH2:9])=[CH:5][CH:4]=1.[OH-].[Na+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>C1C=CC=CC=1.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:7](=[O:10])[CH2:8][NH:9][C:17](=[O:18])[CH2:16][Cl:15])=[CH:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 27982112-Amino-1-(4-chlorophenyl)ethan-1-one hydrochloride

Produkt 1

HCID 53685377N-(4-chlorophenacyl) chloroacetamideAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a well stirred suspension of 20.6 g of 4-chlorophenacylamine hydrochloride in 70 ml of benzene and 70 ml of water which was cooled to below 7° C were added simultaneously 110 ml of 2N NaOH solution and 12.4 g of chloroacetyl chloride dissolved in 30 ml of benzene. After the addition was complete, the reaction mixture was warmed to room temperature and stirred at room temperature for 3 hours. At the end of this period, the formed precipitate was filtered, and the benzene layer was separated. The aqueous layer was extracted twice with 50 ml of benzene. The combined benzene layer was dried over anhydrous sodium sulfate, and evaporated to dryness. The residue together with the precipitate obtained above was combined and recrystallized from ethanol to give 14.1 g (57 percent) of N-(4-chlorophenacyl) chloroacetamide.

Aufarbeitung

  1. temperaturewas cooled to below 7° C
  2. additionAfter the addition
  3. stirringstirred at room temperature for 3 hours
  4. filtrationAt the end of this period, the formed precipitate was filtered
  5. customthe benzene layer was separated
  6. extractionThe aqueous layer was extracted twice with 50 ml of benzene
  7. dry with materialThe combined benzene layer was dried over anhydrous sodium sulfate
  8. customevaporated to dryness
  9. customThe residue together with the precipitate obtained
  10. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-83d612f9492a4e9883641d30e30df7d7
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04101660

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