4-Chloro-3-nitrotoluene → 2,5-Dimethyl-3-(4-methyl-2-nitro-phenylsulfanyl)-furan

HRID 2358645Notes

Reaction equation

HRID 2358645 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]1[O:14][C:15]([CH3:19])=[CH:16][C:17]=1[SH:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:12][C:13]1[O:14][C:15]([CH3:19])=[CH:16][C:17]=1[S:18][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 69764-Chloro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 415692,5-Dimethyl-3-furanthiol

Product 1

HCID 684583602,5-Dimethyl-3-(4-methyl-2-nitro-phenylsulfanyl)-furanYield 113.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-Chloro-4-methyl-2-nitro-benzene (2.00 g, 11.7 mmol), 2,5-Dimethyl-furan-3-thiol (1.50 g, 11.7 mmol), and K2CO3 (3.233 g, 23.4 mmol) heated in DMF at 100° C. for 4 hrs. Reaction mixture was then cooled to room temperature and diluted with water and extracted with ethyl acetate. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (3.5 g, 85%).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c43dd555f3ff46a1a31212c224de09cf
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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