1-Bromooctane → 2-Octylthio-4,5-diphenylimidazole

HRID 1376351Notes

Reaction equation

HRID 1376351 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([SH:18])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:20]([S:18][C:9]1[NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 178527825HCID 178527825, compound

Product 1

HCID 229164132-Octylthio-4,5-diphenylimidazoleYield 53%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4,5-diphenyl-2-imidazolethiol (2.5 g), 8-bromooctane (3.8 g), anhydrous potassium carbonate (13.7 g) and dry butanone (60 ml) was stirred at reflux for 2 h. The cooled reaction mixture was filtered to remove solid and the flitrate was evaporated to dryness. The residue was mixed with hexane and the resulting precipitate was collected by filtration. Recrystallisation from ethanol and water gave 2-octylthio-4,5-diphenylimidazole (1.9 g, 53%) as a white solid, m.p. 133°-4°.

Workup

  1. temperatureat reflux for 2 h
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto remove solid
  5. customthe flitrate was evaporated to dryness
  6. additionThe residue was mixed with hexane
  7. filtrationthe resulting precipitate was collected by filtration
  8. customRecrystallisation from ethanol and water

Sources & evidence

ORD record
ord-b02f1a7711dd4b5c9f87b1c1763e97b5
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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