2-Bromoethyl ethyl ether → HCID 22272806, compound

HRID 1064810Notes

Reaction equation

HRID 1064810 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5]Br)[CH3:2].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[S:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH:28][C:29]2[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[C:31]([OH:38])[C:30]=2[CH:39]([CH3:41])[CH3:40])=[O:27])[CH2:21][CH2:20]1>[F-].[K+].C(#N)C>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[S:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH:28][C:29]2[C:34]([CH:35]([CH3:36])[CH3:37])=[CH:33][CH:32]=[C:31]([O:38][CH2:2][CH2:1][O:3][CH2:4][CH3:5])[C:30]=2[CH:39]([CH3:41])[CH3:40])=[O:27])[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 611412-Bromoethyl ethyl etherHCID 222726162-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide

Product 1

HCID 22272806HCID 22272806, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 522689Potassium FluorideCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Bromoethyl ethyl ether (2 ml) and potassium fluoride catalyst carried on alumina (40 wt %, 225 mg, 1.51 mmol) were added to a solution of 2-[4-[2-(benzoxazol-2ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide (150 mg, 0.30 mmol) in acetonitrile (3 ml) followed by stirring for 41 hours. The catalyst was filtered off and the filtrate was diluted with water and extracted with ethyl acetate. The organic layer was washed with a sodium chloride solution and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a preparative thin layer chromatography (developing solvent, chloroform:ammonia-saturated methanol=20:1) and the resulting crude crystals were recrystallized from ethyl acetate-hexane to provide 120 mg (yield 70%) of the desired compound as colorless powdery crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe filtrate was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by a preparative thin layer chromatography (developing solvent, chloroform:ammonia-saturated methanol=20:1)
  8. customthe resulting crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a97242acab8944488b23ce99ae3e3ffe
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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