Benzonitrile, 4-chloro-3-nitro- → HCID 29106440, compound

HRID 2197808Notes

Reaction equation

HRID 2197808 reaction equation
[C:1]1([S-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].Cl[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]>CN(C=O)C.CCOC(C)=O>[N+:18]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:10]=1[S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:14]#[N:15])([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 4110039Sodium benzenethiolate

Product 1

HCID 29106440HCID 29106440, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium thiophenolate (16.29 g, 123.3 mmol) in 150 mL of DMF was heated at 100° C. with 4-chloro-3-nitrobenzonitrile (15.0 g, 82.2 mmol) with stirring for 24 hours. Cooled to room temperature and diluted with EtOAc. Washed with water and dried the organic layer over MgSO4. Filtered and concentrated under vacuum giving the title compound, which was purified by silica gel column chromatography eluting with 5% EtOAc/hexane giving a yellow solid (4.0 g, 19%).

Workup

  1. washWashed with water
  2. dry with materialdried the organic layer over MgSO4
  3. filtrationFiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d68983be8a5448c4b179cd162d93b76b
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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