Potassium Hydroxide → HCID 6476762, compound

HRID 1195147Notes

Reaction equation

HRID 1195147 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]\[CH2:4][SH:5].[OH-].[K+].Cl[CH:15]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CO.C(O)C>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[CH:15]([S:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 6365572(E)-3,7-Dimethylocta-2,6-diene-1-thiolHCID 124607821-[2-Chloro-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole

Product 1

HCID 6476762HCID 6476762, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of (E)-3,7-dimethylocta-2,6-dienylmercaptan (1.00 g=5.9 mmol) in methanol (40 ml) was added potassium hydroxide (0.33 g=5.8 mmol) and 1-chloro-1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethane (1.62 g=5.9 mmol) in ethanol at room temperature, and then the reaction mixture was refluxed for 90 minutes. After cooling, the methanol was evaporated, and then the residue was diluted with chloroform. The chloroform layer was washed with water, followed by drying over anhydrous sodium sulfate. Concentration followed by column chromatography on silica gel (ethyl acetate:hexane=2:3) gave 1.32 g of Compound 10 as a colorless oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 90 minutes
  2. temperatureAfter cooling
  3. customthe methanol was evaporated
  4. additionthe residue was diluted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialby drying over anhydrous sodium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-10baf165870b4d5da61e6c5298cf9bdb
Source dataset
uspto-grants-1992_05
Patent number
US05110826

Reaction notes

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