Réaction #931

ord-942c876021324f25bb9887685a674993

Équation de réaction

O
water
N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-]
2,6-dinitrobenzonitrile
O=C([O-])[O-].[K+].[K+]
K2CO3
Cc1cc(C)cc(S)c1
3,5-dimethylthiophenol
→
Cc1cc(C)cc(Sc2cccc([N+](=O)[O-])c2C#N)c1
2-[(3,5-dimethylphenyl)thio]-6-nitrobenzonitrile

Réactifs

O
water
N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-]
2,6-dinitrobenzonitrile
O=C([O-])[O-].[K+].[K+]
K2CO3
Cc1cc(C)cc(S)c1
3,5-dimethylthiophenol

Réactifs

Aucun

Solvants

CN(C)C=O
DMF
CN(C)C=O
DMF

Conditions de réaction

Température
0°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.STIRRINGAfter stirring an additional 30 min
  2. 2
    workup.STIRRINGstirred for 1 hr
  3. 3
    FiltrationThe solid was collected by vacuum filtration

Mode opératoire

A mixture of 2,6-dinitrobenzonitrile (1.4 g 7.2 mmol) and K2CO3 (1.1 g, 7.9 mmol) in 10 ml of DMF was chilled to 0° C. A solution of 3,5-dimethylthiophenol (1.1 g 0.0079 mmol) in 10 ml of DMF, was added dropwise over 30 min with stirring under nitrogen. After stirring an additional 30 min, the reaction mixture was poured into 150 ml of water and stirred for 1 hr. The solid was collected by vacuum filtration. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 1.64 g (80%) of 2-[(3,5-dimethylphenyl)thio]-6-nitrobenzonitrile: mp 155°-156° C.

Source

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