Reaction #931

ord-942c876021324f25bb9887685a674993

Reaction equation

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

Reactants

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

Reagents

None

Solvents

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

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  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

Procedure

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.v1Patent: US05723452uspto-grants-1998_03