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

HRID 2358528Notes

Reaction equation

HRID 2358528 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 Na2 SO4. 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. customdried the organic layer over Na2 SO4
  3. filtrationFiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-80f4f498812d4d2ba331c4cac2c00ec4
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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