Potassium Carbonate → HCID 10479124, compound

HRID 265421Notes

Reaction equation

HRID 265421 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-:36].[K+].[K+]>CC(=O)CC>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:8]2=[O:36])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 5160865HCID 5160865, compound

Product 1

HCID 10479124HCID 10479124, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1,4,5 triphenylimidazole (6.24 g), ethyl 6-bromohexanoate (13.38 g), potassium carbonate (13.2 g) and 2-butanone was stirred at reflux for 6 hours. The mixture was filtered, and the filtrate was evaporated. The residue was chromatographed on silica gel eluted with ethanol-hexane to give the title compound (5.61 g) m.p. 104°-106° C. Found: C, 76.35; H, 6.58; N, 6.07%; (C29H30N2O2O3) Requires: C, 76.63; H, 6.65; N, 6.16%

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was chromatographed on silica gel
  5. washeluted with ethanol-hexane

Sources & evidence

ORD record
ord-2335dc5a758a4b3fb0b2d535e89f700e
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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