4-Chloro-3-nitrotoluene → 4-Methyl-2-nitro-1-phenylsulfanyl-benzene

HRID 607143Notes

Reaction equation

HRID 607143 reaction equation
[C:1]1([S-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].Cl[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18]>CN(C=O)C.C(Cl)Cl>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

5

Reactant 2

HCID 69764-Chloro-3-nitrotolueneHCID 4110039Sodium benzenethiolate

Product 1

HCID 596452024-Methyl-2-nitro-1-phenylsulfanyl-benzeneYield 87.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of sodium thiophenolate (3.96 g, 30 mmol) in 60 mL of DMF was heated at 50° C. with 4-chloro-3-nitrotoluene (2.65 mL, 20 mmol) with stirring for 2 days. Cooled to room temperature and diluted with CH2Cl2. Washed with water and dried the organic layer over Na2SO4. Filtered and concentrated under vacuum giving the title compound (4.29 g, 87%) 1H NMR (300 MHz, CDCl3) δ ppm: 2.36 (s, 3H) 6.76 (d, J=8.09 Hz, 1H) 7.16 (d, J=8.46 Hz, 1H) 7.45 (m, 3H) 7.58 (m, 2H) 8.03 (s, 1H).

Workup

  1. washWashed with water
  2. dry with materialdried the organic layer over Na2SO4
  3. filtrationFiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e3a814cf147e4b0294817314f3a9c947
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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