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

HRID 1806110Notes

Reaction equation

HRID 1806110 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-5e3b7750130b4cf689de4ab764847afd
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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