Thiophenol → HCID 59598389, compound

HRID 2359697Notes

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

Conditions

Temperature: 100 °C

Procedure

In a 25 mL sealed tube under N2, were dissolved 4-chloro-7-methoxyquinoline (1.00 g, 5.16 mmol), thiophenol (0.528 ml, 5.16 mmol) and cesium carbonate (2.52 g, 7.75 mmol) in 5 mL of DMSO then heated at 100° C. After 2 h, the crude reaction mixture was directly purified by MPLC (ISCO, dichloromethane:MeOH 100:0 to 90:10) to afford 7-methoxy-4-(phenylthio)quinoline (1.32 g, 95.6% yield) as an off-white solid. MS (ESI pos. ion) m/z: 268 (MH+). Calc'd exact mass for C16H13NOS: 267. 1H NMR (400 MHz, CDCl3): 8.49 (d, J=4.93 Hz, 1H), 8.13 (d, J=9.22 Hz, 1H), 7.56-7.62 (m, 2H), 7.45-7.53 (m, 4H), 7.23-7.29 (m, 1H), 6.68 (d, J=4.93 Hz, 1H), 3.98 (s, 3H).

Workup

customIn a 25 mL sealed tube under N2
customthe crude reaction mixture
customwas directly purified by MPLC (ISCO, dichloromethane:MeOH 100:0 to 90:10)

Sources & evidence

ORD record: ord-8001f73f567e445d8ba326beb59df2c9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685983B2

Reaction notes

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