Acetone → HCID 68117511, compound

HRID 259275Notes

Reaction equation

HRID 259275 reaction equation
Cl[CH:2]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=1.[C:26](=[O:29])([O-:28])[O-].[K+].[K+].CC(C)=[O:34]>>[C:11]([OH:10])(=[O:34])[C:26]([OH:28])=[O:29].[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH:2]([S:25][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH2:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 13316653HCID 13316653, compound

Product 1

HCID 68117511HCID 68117511, compound

Procedure

The chloro compound, i.e., 1-[2'-chloro-3'-(4"-chlorophenoxy)propyl]imidazole (2.1g.), is then heated under reflux with 1.5 g. p-chlorothiophenol and 1.4 g. of anhydrous potassium carbonate in 50 ml. of acetone. After stirring for 12 hours the solvent is removed and water is added to the residue. The resultant aqueous phase is then extracted with ether and the ether extracts washed with water, dried over magnesium sulfate and acidified with oxalic acid. The product which precipitates is filtered off and recrystallized from ethyl acetate to yield 1-[3'-(4"-chlorophenoxy)-2'-(4"-chlorophenylthio)propyl]imidazole oxalate, m.p. 81°-85.5° C.

Workup

  1. temperatureunder reflux with 1.5 g
  2. customis removed
  3. additionwater is added to the residue
  4. extractionThe resultant aqueous phase is then extracted with ether
  5. washthe ether extracts washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe product which precipitates
  8. filtrationis filtered off
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9d13972c3be8420eaadec8e2963e8909
Source dataset
uspto-grants-1977_07
Patent number
US04036970

Reaction notes

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