Reacción #2186222

ord-2a77e91c6c32445498e64bc6d139404f

Ecuación de reacción

N#Cc1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(N)c1S(=O)(=O)C(F)(F)F
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-1 H-pyrazole-3-carbonitrile
O=S(=O)(O)O
sulfuric acid
NC(=O)c1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(N)c1S(=O)(=O)C(F)(F)F
title compound
Rendimiento 83.0%
NC(=O)c1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(N)c1S(=O)(=O)C(F)(F)F
5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-1H-pyrazole-3-carboxylic acid amide
Rendimiento 83.0%

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónthe precipitate filtered off
  2. 2
    Lavadowashed with water
  3. 3
    Otroair-dried
  4. 4
    OtroPurification by flash chomatography (silica, chloroform)

Procedimiento

A stirred mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-1 H-pyrazole-3-carbonitrile (1.06 g, 2.21 mmol) and concentrated sulfuric acid (1 ml) was heated to 100° C. for 3 hours. The cooled mixture was added to ice water and the precipitate filtered off, washed with water and air-dried. Purification by flash chomatography (silica, chloroform) gave the title compound (0.869 g, yield 83%) as off-white crystals, mp 217° C., 1H NMR (DMSO-d6): 7.39 (bs, 2H, NH2), 7.57 and 7.78 (bs, 2H, C(O)NH2), and 8.25 (s, 2H, Ar—H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07569516B2uspto-grants-2009_08