Hydrochloric Acid → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(6-phenylhexyl)-

HRID 1416049Notes

Reaction equation

HRID 1416049 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[I-].[K+].[Cl:16][C:17]1[CH:18]=[C:19]([S:24][C:25]2[NH:29][C:28]([CH2:30][O:31]CC3C=CC(OC)=CC=3)=[N:27][C:26]=2[CH:41]([CH3:43])[CH3:42])[CH:20]=[C:21]([Cl:23])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.C(O)C.CN(C)C=O>[Cl:23][C:21]1[CH:20]=[C:19]([S:24][C:25]2[N:29]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:28]([CH2:30][OH:31])=[N:27][C:26]=2[CH:41]([CH3:43])[CH3:42])[CH:18]=[C:17]([Cl:16])[CH:22]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5224111-Chloro-6-phenylhexaneHCID 178491401HCID 178491401, compound

Product 1

HCID 4740411H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(6-phenylhexyl)-Yield 37.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To dimethylformamide was added 99 mg of 1-chloro-6-phenylhexane and 152 mg of potassium iodide under ice-cooling, the mixture was allowed to warm up to room temperature and stirred for 20 minutes. Then, 200 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (101b)was added, followed by addition of 126 mg of potassium carbonate. Then, the mixture was warmed up to 50° C. and allowed to react for 6 hours. After completion of the reaction, the mixture was diluted with water, extracted with diethyl ether, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. To thus-obtained oil were added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, and the mixture was stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1)to give 81 mg of Compound I-125 (yield 37%).

Workup

  1. temperaturecooling
  2. temperatureThen, the mixture was warmed up to 50° C.
  3. customto react for 6 hours
  4. customAfter completion of the reaction
  5. extractionextracted with diethyl ether
  6. dry with materialthe extract was dried over sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customTo thus-obtained oil
  9. stirringthe mixture was stirred at 90° C. for 2 hours
  10. customAfter completion of the reaction
  11. distillationthe solvent was distilled off under reduced pressure
  12. additionan aqueous sodium hydrogen carbonate solution was added
  13. extractionextracted with ethyl acetate
  14. dry with materialThe extract was dried over sodium sulfate
  15. distillationthe solvent was distilled off under reduced pressure
  16. customThe residue was purified by silica gel chromatography (hexane

Sources & evidence

ORD record
ord-c8398caab0fe40efb2520d55dee25cb2
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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