Chloroacetyl chloride → N-(2-Anilinophenyl)-2-chloroacetamide

HRID 1709632

Reaktionsgleichung

Reaktionsgleichung von HRID 1709632
[C:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)(Cl)Cl.O>[Cl:22][CH2:23][C:24]([NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:25]

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 68297N-Phenyl-o-phenylenediamine

Produkt 1

HCID 14819969N-(2-Anilinophenyl)-2-chloroacetamideAusbeute 106 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In 100 ml of chloroform, 10.4 g of N-phenyl-1,2-benzenediamine and 12.1 g of triethylamine were dissolved, and the mixture was cooled to -5° C. to 0° C., and then 13.6 g of chloroacetyl chloride was added dropwise thereto, holding the temperature of the mixture at not higher than 20° C. The reaction nearly went to completion when the addition was finished. After stirring for further 30 minutes, the reaction mixture was diluted with 50 ml of water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate and then the solvent is evaporated under reduced pressure. The resulting solid was recrystallized from ethanol to give 15.6 g of crystals having a melting point of 112° C. to 113° C. Yield: 60.0%.

Aufarbeitung

  1. temperaturethe mixture was cooled to -5° C. to 0° C.
  2. customhigher than 20° C
  3. customThe reaction
  4. additionthe addition
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent is evaporated under reduced pressure
  9. customThe resulting solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-37906dc48d31413d9bf4a7aee1b72f6b
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04950667

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