Réaction #929

ord-9c0049ffd5bd4c2597bd8dc1da4f9125

Équation de réaction

N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-]
2,6-dinitrobenzonitrile
Sc1ccccc1
thiophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
c1ccncc1
Pyridine
N#Cc1c(Sc2ccccc2)cccc1[N+](=O)[O-]
2-nitro-6-(phenylthio)benzonitrile
Rendement 89.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationThe yellow precipitate was collected by filtration
  2. 2
    Lavagewashed with 1N NaOH, water
  3. 3
    Autredried

Mode opératoire

An ice water bath-cooled mixture of 2.0 g (0.01 mol) of 2,6-dinitrobenzonitrile (Lancaster Synthesis, Inc., Windham, N.H. 03087), 1.06 ml (0.01 mol) of thiophenol, and 1.44 g (0.01 mol) of anhydrous K2CO3 in 50 mL of DMF was stirred for 0.5 h. Pyridine was added to the reaction mixture until it became basic, and was followed by the addition of approximately 100 mL of H2O. The yellow precipitate was collected by filtration, washed with 1N NaOH, water and dried to give 1.94 g (89%) of 2-nitro-6-(phenylthio)benzonitrile as a yellow solid: mp 106°-107° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05723452uspto-grants-1998_03