4-Chloro-3-nitrotoluene → N-[3-Fluoro-4-(4-methyl-2-nitro-phenylsulfanyl)-phenyl]-acetamide

HRID 2358581Notes

Reaction equation

HRID 2358581 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].ClC1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]

Participants

5

Reactant 2

HCID 69764-Chloro-3-nitrotolueneHCID 68459196N-(3-Fluoro-4-methylsulfanyl-phenyl)-acetamide

Product 1

HCID 68460909N-[3-Fluoro-4-(4-methyl-2-nitro-phenylsulfanyl)-phenyl]-acetamideYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 39c (1.00 g, 5.0 mmol) and t-BuSNa (1.88 g, 15.1 mmol) in anhydrous DMF (10 mL) was heated at 160° C. for 4 hours under N2 flow, and then cooled to room temperature. To the reaction mixture was added 1-chloro-4-methyl-2-nitrobenzene (2.36 mL, 17.6 mmol) at room temperature and then the mixture was heated at 80° C. for 4 hours under N2 flow. The mixture was diluted with H2O and then extracted with EtOAc. The extract washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by silica gel column chromatography eluting with 2:1 EtOAc/hexane to give the title compound as yellow crystals (1.04 g, 65%).

Workup

  1. temperaturethe mixture was heated at 80° C. for 4 hours under N2 flow
  2. extractionextracted with EtOAc
  3. washThe extract washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 2:1 EtOAc/hexane

Sources & evidence

ORD record
ord-b236311b837e499780595771d5a450b6
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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