Pyridine → 2-Nitro-6-(phenylthio)benzonitrile

HRID 833

Reaction equation

HRID 833 reaction equation
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>CN(C=O)C.O>[N+:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([S:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]=1[C:6]#[N:7])([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 520718Dinitrobenzonitrile

Product 1

HCID 151982412-Nitro-6-(phenylthio)benzonitrileYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. filtrationThe yellow precipitate was collected by filtration
  2. washwashed with 1N NaOH, water
  3. customdried

Sources & evidence

ORD record
ord-9c0049ffd5bd4c2597bd8dc1da4f9125
Source dataset
uspto-grants-1998_03
Patent number
US05723452

Linked notes

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