Reacción #2045093

ord-457ecc6eabfb4774b861b707817d9960

Ecuación de reacción

O=C(CBr)c1ccc(Cl)cc1
2-bromo-1-(4-chlorophenyl)ethanone
CC#N
acetonitrile
Cl.NCC(=O)c1ccc(Cl)cc1
2-amino-1-(4-chlorophenyl)ethanone hydrochloride
Rendimiento 50.0%

Condiciones de reacción

Temperatura
105°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas heated
  2. 2
    OtroThe formed sodium bromide was removed by filtration
  3. 3
    Concentraciónthe filtrate concentrated in vacuo
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in ethanol (2.5 mL per mmol)
  5. 5
    workup.ADDITIONconc. aq. hydrochloric acid (0.9 mL per mmol) added at ambient temperature
  6. 6
    Filtraciónwere filtered off
  7. 7
    Lavadowashed with ethanol (1×0.5 mL per mmol)
  8. 8
    OtroDrying of the solids

Procedimiento

A mixture of 2-bromo-1-(4-chlorophenyl)ethanone (1.0 eq.) and NaN(CHO)2 (1.1 eq.) in acetonitrile (1.5 mL per mmol) was heated to reflux for 4 h at 105° C. ext. temperature. The formed sodium bromide was removed by filtration and the filtrate concentrated in vacuo. The residue was dissolved in ethanol (2.5 mL per mmol) and conc. aq. hydrochloric acid (0.9 mL per mmol) added at ambient temperature. After stirring for 72 h at room temperature the solids were filtered off and washed with ethanol (1×0.5 mL per mmol). Drying of the solids afforded 2-amino-1-(4-chlorophenyl)ethanone hydrochloride in ca. 50% yield that was used in the next step without purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08410023B2uspto-grants-2013_04