Potassium Carbonate → 2-(4-Methyl-2-nitro-phenylsulfanyl)-pyridine

HRID 2197989Notes

Reaction equation

HRID 2197989 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 713468894-Methyl-2-nitrophenyl trifluoromethanesulfonateHCID 178418616HCID 178418616, compound

Product 1

HCID 684584452-(4-Methyl-2-nitro-phenylsulfanyl)-pyridineYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from the reaction of trifluoro-methanesulfonic acid 4-methyl-2-nitro-phenyl ester (3.50 g, 12.27 mmol) reacting with pyridine-2-thiol (2.046 g, 18.41 mmol), and K2CO3 (2.968 g, 21.48 mmol) in DMF at 100° C. for 16 h the reaction mixture was then cooled to room temperature and diluted with water, extracted with EtOAc Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (2.52 g, 78%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialDried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4821244556774aef972a756914925482
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

Loading…