Thiophenol → HCID 59598389, compound

HRID 1013734Notes

Reaction equation

HRID 1013734 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([S:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 106078294-Chloro-7-methoxyquinoline

Product 1

HCID 59598389HCID 59598389, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube under N2 was charged with 4-chloro-7-methoxyquinoline (1.00 g, 5.16 mmol), thiophenol (0.528 ml, 5.16 mmol), cesium carbonate (2.52 g, 7.75 mmol) and DMSO (5 mL). The mixture was heated at 100° C. for 2 hrs. The crude reaction mixture was directly purified by silica gel chromatography using 0-10% CH2Cl2:MeOH to afford 7-methoxy-4-(phenylthio)quinoline as a off-white solid. MS: M+H+=268.0.

Workup

  1. customThe crude reaction mixture
  2. customwas directly purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2aa6e7f15d843b09ef6ad5d3c0ab8cc
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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