Iodoethane → HCID 12807880, compound

HRID 325648Notes

Reaction equation

HRID 325648 reaction equation
[CH2:1](I)[CH3:2].[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[CH2:15][S:16]([CH3:19])(=[O:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:4])[C:6]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178504870HCID 178504870, compound

Product 1

HCID 12807880HCID 12807880, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl iodide (2.93 g.) was added to a stirred mixture of 4-hydroxy-3-methylsulphonylmethylquinoline (1.93 g.), anhydrous potassium carbonate (2.3 g.) and 2-butanone (80 ml.) The mixture was boiled under reflux for 24 hours and the solvent was evaporated. The mixture was diluted with water (200 ml.) and left overnight. The mixture was filtered and the filtrate evaporated to dryness to give a white solid. This was purified by high pressure liquid chromatography over silica gel using ethyl acetate:isopropanol 9:1 as the eluant at a flow rate of 200 ml. per minute. There was obtained the novel compound 1-ethyl-3-methylsulphonylmethyl-4-quinolone, m.p. 162°-164°.

Workup

  1. temperatureunder reflux for 24 hours
  2. customthe solvent was evaporated
  3. additionThe mixture was diluted with water (200 ml.)
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated to dryness
  6. customto give a white solid
  7. customThis was purified by high pressure liquid chromatography over silica gel

Sources & evidence

ORD record
ord-84b2b4b4c6084bd8b26e02dcd7807cef
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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