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

HRID 846671Notes

Reaction equation

HRID 846671 reaction equation
[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]

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 81011-BromohexaneHCID 157249697-hydroxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one

Product 1

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

Procedure

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.

Workup

  1. temperaturerefluxed for 33 hours
  2. temperatureto cool
  3. filtrationThen insoluble matter was filtered
  4. customThe solvent was evaporated off under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-33607370258d4c6eaa76f09e5f211e59
Source dataset
uspto-grants-1992_08
Patent number
US05137909

Reaction notes

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