Reacción #1478574

ord-16c0fd29e0ed49c7ae84da016654edbe

Ecuación de reacción

Nc1ccc([N+](=O)[O-])cc1
p-nitroaniline
O=C([O-])[O-].[Ca+2]
calcium carbonate
NC(=O)CCl
chloroacetamide
NC(=O)CNc1ccc([N+](=O)[O-])cc1
pure product
Rendimiento 58.0%
NC(=O)CNc1ccc([N+](=O)[O-])cc1
2-(4-nitrophenylamino)acetamide
Rendimiento 58.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas refluxed for 42 hours
  2. 2
    FiltraciónThe resulting mixture was filtered while hot and
  3. 3
    Temperaturato cool
  4. 4
    Filtraciónthe crystals were filtered off by suction
  5. 5
    Lavadowashed with absolute ethanol
  6. 6
    OtroAfter drying
  7. 7
    Otro87.9 g of crude product were obtained
  8. 8
    OtroAfter two recrystallizations from acetonitrile

Procedimiento

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.).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07338536B2uspto-grants-2008_03