Potassium Iodide → 7-hexyloxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one

Reaktionsgleichung

[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[C:11](=[O:21])[C:12]([CH3:20])([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[S:13][C:6]3=[CH:5][C:4]=2[CH:3]=1.[CH2:22](Br)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[I-].[K+]>>[CH2:22]([O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[C:11](=[O:21])[C:12]([CH3:20])([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[S:13][C:6]3=[CH:5][C:4]=2[CH:3]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

Edukt 3

HCID 4875Potassium Iodide

HCID 81011-Bromohexane

HCID 157249697-hydroxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one

Produkt 1

HCID 157249707-hexyloxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-oneAusbeute 93 %

Versuchsvorschrift

To a solution of 7-hydroxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one (2.86 g), n-hexyl bromide (1.76 g) and a small amount of potassium iodide, and the mixture was heated and refluxed for 33 hours. The reaction mixture was allowed to cool. Then insoluble matter was filtered. The solvent was evaporated off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate=9:1) to give 3.4 g (yield: 93%) of 7-hexyloxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3-(2H)-one.