Potassium Carbonate → HCID 20329506, compound

HRID 2057944Notes

Reaction equation

HRID 2057944 reaction equation
Cl.Cl[CH:3]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[SH:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27][CH:3]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80599o-ChlorothiophenolHCID 23457691HCID 23457691, compound

Product 1

HCID 20329506HCID 20329506, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-[2-chloro-4-(4-methoxyphenyl)-n-butyl]imidazole hydrochloride (prepared from 2.00 g. of alcohol as in Preparation C), 2-chlorothiophenol (2.80 g) and anhydrous potassium carbonate (2.70 g) in acetone (50 ml) was heated under reflux with stirring overnight. After removal of the solvent under reduced pressure, ether (150 ml) was added and the extract washed with water (2×30 ml) and dried (MgSO4) and the solvent removed to afford 1-[2-(2-chlorophenylthio)-4-(4-methoxyphenyl)-n-butyl]imidazole. Dropwise addition of 70% nitric acid (d-1.42) to an ethereal solution of this material until precipitation was complete gave the nitrate salt of 1-[2-(2-chlorophenylthio)-4-(4-methoxyphenyl)-n-butyl]imidazole, recrystallized from acetone/ethyl acetate as colorless microcrystals (3.10 g), mp 131.5°-133.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customAfter removal of the solvent under reduced pressure, ether (150 ml)
  4. additionwas added
  5. washthe extract washed with water (2×30 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed

Sources & evidence

ORD record
ord-f8a316d5f0714ebea384a0363aa1b79e
Source dataset
uspto-grants-1980_07
Patent number
US04213991

Reaction notes

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