Potassium ethylxanthate → HCID 12460786, compound

HRID 441430Notes

Reaction equation

HRID 441430 reaction equation
Cl.Cl[CH:3]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[O:18]([CH2:22][CH3:23])[C:19]([S-:21])=[S:20].[K+]>C(O)C>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[CH:3]([S:21][C:19]([O:18][CH2:22][CH3:23])=[S:20])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 124607831H-Imidazole, 1-[2-chloro-2-(2,4-dichlorophenyl)ethyl]-, hydrochloride (1:1)

Product 1

HCID 12460786HCID 12460786, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Twenty grams of 1-(β, 2,4-trichlorophenethyl)imidazole hydrochloride was added to 300 milliliters (ml) of absolute ethanol and 25 grams of anhydrous potassium ethyl xanthate. The mixture was stirred at room temperature for about 3 days until the reaction was complete as indicated by thin layer chromatography. The solvent was removed, water added and the product extracted with ether. The extracts were washed with water, dried over magnesium sulfate and the ether evaporated. The resulting oil was purified by chromatography on silicia gel eluting with 15% acetone in dichloromethane. The resulting oil was then dissolved in ether and an ethereal solution of oxalic acid was added dropwise until precipitation was complete. Recrystallization of the precipitate from acetone provides the oxalate salt of 1-[2,4-dichloro-β-(ethoxythiocarbonylthio)phenethyl]imidazole as a white solid having a melting point of 122.5°-124° C. (foaming).

Workup

  1. customThe solvent was removed
  2. additionwater added
  3. extractionthe product extracted with ether
  4. washThe extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe ether evaporated
  7. customThe resulting oil was purified by chromatography on silicia gel
  8. washeluting with 15% acetone in dichloromethane
  9. dissolutionThe resulting oil was then dissolved in ether
  10. additionan ethereal solution of oxalic acid was added dropwise until precipitation
  11. customRecrystallization of the precipitate from acetone

Sources & evidence

ORD record
ord-5194483cd0344087936e5915669b5c6a
Source dataset
uspto-grants-1977_08
Patent number
US04039677

Reaction notes

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