Diethyl Ether → 1-(5-Phenyl-pentyl)-3-(2-trifluoromethyl-phenylsulfanyl)-quinolinium iodide

HRID 2063933Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.[I:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCOCC>C1S(=O)(=O)CCC1>[I-:22].[C:28]1([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][N+:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:19]=[C:10]([S:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:20])([F:1])[F:21])[CH:11]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(2-trifluoromethyl-phenylsulfanyl)-quinoline (370 mg, 1.21 mmol), (5-iodo-pentyl)-benzene (520 mg, 1.9 mmol) in tetramethylene sulfone (1 mL) was sealed in a tube and heated at 100° C. for 12 h. Ether (10 mL) was added resulting in a solid product. The product was crystallized from MeOH-Et2O to yield 1-(5-phenyl-pentyl)-3-(2-trifluoromethyl-phenylsulfanyl)-quinolinium iodide (632 mg, 90%). Mp 227-229° C.

Workup

customwas sealed in a tube
customresulting in a solid product
customThe product was crystallized from MeOH-Et2O

Sources & evidence

ORD record: ord-70f5952758d34c2b8226606113ee0129
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288410B2

Reaction notes

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