Chloroacetamide → N~2~-(4-Nitrophenyl)glycinamide

HRID 1391392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391392
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Ca+2].Cl[CH2:17][C:18]([NH2:20])=[O:19]>O.C(O)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:17][C:18]([NH2:20])=[O:19])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 6580ChloroacetamideHCID 74754-NitroanilineHCID 10112Calcium Carbonate

Produkt 1

HCID 23104345N~2~-(4-Nitrophenyl)glycinamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A mixture of p-nitroaniline (55.2 g, 0.4 mol), calcium carbonate (80 g) and chloroacetamide (149.6 g, 1.6 mol) in 350 ml of water/ethanol (1/1) was refluxed for 42 hours. The resulting mixture was filtered while hot and allowed to cool, and the crystals were filtered off by suction, reslurried in water and then washed with absolute ethanol. After drying, 87.9 g of crude product were obtained. After two recrystallizations from acetonitrile, 45.3 g of pure product were obtained (melting point=178° C.).

Aufarbeitung

  1. temperaturewas refluxed for 42 hours
  2. filtrationThe resulting mixture was filtered while hot and
  3. temperatureto cool
  4. filtrationthe crystals were filtered off by suction
  5. washwashed with absolute ethanol
  6. customAfter drying
  7. custom87.9 g of crude product were obtained
  8. customAfter two recrystallizations from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-16c0fd29e0ed49c7ae84da016654edbe
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338536B2

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