Cesium carbonate → Methyl 4-(2-nitropyridin-3-ylthio)benzoate

HRID 911863Notes

Reaction equation

HRID 911863 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl[C:13]1[C:14]([N+:19]([O-:21])=[O:20])=[N:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[N+:19]([C:14]1[C:13]([S:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)=[CH:18][CH:17]=[CH:16][N:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 237573Methyl 4-sulfanylbenzoateHCID 5549883-Chloro-2-nitropyridine

Product 1

HCID 66995042Methyl 4-(2-nitropyridin-3-ylthio)benzoateYield 84.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Stirred a mixture of methyl 4-mercaptobenzoate (4.46 g, 26.5 mmol), 3-chloro-2-nitropyridine (4.00 g, 25.2 mmol) and cesium carbonate (9.04 g, 27.8 mmol) in DMSO (60 mL) at ambient temperature for 90 minutes. The solution was diluted with water, extracted with EtOAc, dried, and concentrated. The crude solid was suspended in MeOH (80 mL) and triturated for 0.5 hours. The solid was filtered and dried to provide the title compound (6.16 g, 84.1% yield).

Workup

  1. extractionextracted with EtOAc
  2. customdried
  3. concentrationconcentrated
  4. customtriturated for 0.5 hours
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-cfd6ca5700404f3693e323e222a338bd
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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