Reacción #4331

ord-6690a163904649839ee51f83c59f74e3

Ecuación de reacción

CC(=O)O
acetic acid
O=N[O-].[Na+]
sodium nitrite
O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1
2,5-difluoro-N-benzenesulphonylaniline
O=[N+]([O-])O
nitric acid
→
O=[N+]([O-])c1cc(F)c(NS(=O)(=O)c2ccccc2)cc1F
2,5-difluoro-4-nitro-N-benzenesulphonylaniline

Reactantes

CC(=O)O
acetic acid
—
ice
O=N[O-].[Na+]
sodium nitrite
O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1
2,5-difluoro-N-benzenesulphonylaniline
O=[N+]([O-])O
nitric acid

Reactivos

Ninguno

Disolventes

O
water
O
water

Condiciones de reacción

Temperatura
96°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONare added
  2. 2
    TemperaturaAfter cooling it
  3. 3
    OtroThe expected product precipitates
  4. 4
    FiltraciónAfter being filtered off
  5. 5
    Lavadowashed
  6. 6
    Otrois recrystallized from 250 ml of acetic acid

Procedimiento

To 310 ml of acetic acid diluted with 160 ml of water are added: 1.5 g of sodium nitrite, 0.16 mole (42 g) of 2,5-difluoro-N-benzenesulphonylaniline prepared in the previous stage and 0.94 mole (39 ml) of nitric acid (d=1.52). The reaction mixture is heated to 96° C. for 1 hour. After cooling it is poured onto 1 kg of ice and water. The expected product precipitates. After being filtered off and washed to neutrality it is recrystallized from 250 ml of acetic acid; it melts at 176° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04725283uspto-grants-1988_02