Reacción #163826

ord-c8f766b2c54b40299c95e90185a4edfe

Ecuación de reacción

Nc1ccc(N)cc1
1,4-diaminobenzene
CCN=C=O
ethyl isocyanate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCNC(=O)Nc1ccc(N)cc1
4-(ethylaminocarbonylamino)aniline
Rendimiento 62.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe reaction mixture was partitioned in 1N HCl solution (80 mL)
  2. 2
    ExtracciónThe aqueous layer was extracted with ethyl acetate (4×80 mL)
  3. 3
    OtroThe combined organic layers was dried
  4. 4
    Otroevaporated
  5. 5
    Otrorecrystallized from MeOH/CH2Cl2/hexanes

Procedimiento

A mixture of 1,4-diaminobenzene (4 g, 37 mmol), ethyl isocyanate (1 mL, 12.6 mmol) and potassium carbonate (8.72 g, 63 mmol) in THF (20 mL) was stirred at room temperature overnight. The reaction mixture was partitioned in 1N HCl solution (80 mL) and ethyl acetate (80 mL). The aqueous layer was extracted with ethyl acetate (4×80 mL). The combined organic layers was dried, evaporated, recrystallized from MeOH/CH2Cl2/hexanes to give 4-(ethylaminocarbonylamino)aniline (1.4 g, 62%) as a beige solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08835430B2uspto-grants-2014_09