Sodium Iodide → HCID 17975822, compound

HRID 2108877Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([SH:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Cl:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21]Cl.C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O>[Cl:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][S:13][C:7]1[C:6]2[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

7-Trifluoromethyl-4-quinoline-thiol (2 g, 8.7 mmol) and 2-chloroethyl ether (6.2 g, 43.7 mmol) were charged in a 50 ml round-bottomed flask equipped with a magnetic stirrer. Then Cs2CO3 (2.8 g, 8.7 mmol), NaI (1.3 g, 8.7 mmol), TBABr (1.1 g, 3.5 mmol) and water (15 mL) were added and the reaction mixture was stirred for 1 h at 90° C. The reaction mixture was poured in 100 mL of H2O, extracted with CH2Cl2 (2×100 mL). The organic layer was washed with brine (2×20 mL), dried over MgSO4, filtered and evaporated to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99:1 to 98:2) to give after evaporation 4-[2-(2chloro-ethoxy)-ethylsulfanyl]-7-trifluoromethyl-quinoline 26 (1.9 g, 65% yield) as a colourless oil.

Workup

customequipped with a magnetic stirrer
extractionextracted with CH2Cl2 (2×100 mL)
washThe organic layer was washed with brine (2×20 mL)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated to dryness
customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99:1 to 98:2)
customto give

Sources & evidence

ORD record: ord-670a19cd93ae411187ca65ce8dbee2e2
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514432B2

Reaction notes

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