Benzyl mercaptan → HCID 118094088, Verbindung

Reaktionsgleichung

[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([S:8][C:10]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Versuchsvorschrift

Benzyl mercaptan (6 mL, 50.5 mmol) was added dropwise to a mixture of 5,7-dichloroquinoline (10 g, 50.5 mmol), cesium carbonate (20 g, 60 mmol) and DMF (50 mL) at 0° C. The reaction mixture was allowed to warm to room temperature, stirred for 2 hours and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried with sodium sulfate and concentrated. Purification by column chromatography gave the 5-(benzylthio)-7-chloroquinoline (rf=0.5 in 2:1 hexanes/ethyl acetate) as a crystalline yellow solid. The undesired regioisomer elutes afterwards (rf=0.4 in 2:1 hexanes/ethyl acetate). The reaction is mildly selective for the desired isomer.