Potassium Carbonate → 1-[2-(3,4-Dichlorophenylthio)-4-phenylbutyl]imidazole

HRID 1678987Notes

Reaction equation

HRID 1678987 reaction equation
Cl.Cl[CH:3]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[Cl:18][C:19]1[CH:20]=[C:21]([SH:26])[CH:22]=[CH:23][C:24]=1[Cl:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([S:26][CH:3]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 799643,4-DichlorobenzenethiolHCID 203652681-(2-Chloro-4-phenylbutyl)imidazole hydrochloride

Product 1

HCID 203654361-[2-(3,4-Dichlorophenylthio)-4-phenylbutyl]imidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 600 mg. of 1-(2-chloro-4-phenylbutyl)imidazole hydrochloride, 1.2 g. of 3,4-dichlorothiophenol and 800 mg. of potassium carbonate in 40 ml. of acetone was stirred and refluxed for 4 hours. The solvent was evaporated under vacuum and 50 ml. of water was added. The resulting mixture was extracted with ether and the ether extract was washed with saturated sodium chloride solution, dried and evaporated to afford 1-[2-(3,4-dichlorophenylthio)-4-phenylbutyl]imidazole as an oil. This material was converted to the oxalate salt by treatment with oxalic acid in ether, which salt was recrystallized from acetone/ethyl acetate as colorless flakes (850 mg.), m.p. 145°-147° C.

Workup

  1. additionA mixture of 600 mg
  2. temperaturerefluxed for 4 hours
  3. customThe solvent was evaporated under vacuum and 50 ml
  4. additionof water was added
  5. extractionThe resulting mixture was extracted with ether
  6. extractionthe ether extract
  7. washwas washed with saturated sodium chloride solution
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-72a924ac09ea4a2cb42c21c6be89bf84
Source dataset
uspto-grants-1978_03
Patent number
US04078071

Reaction notes

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