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

HRID 1416055Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:13]([CH2:23][O:24]CC3C=CC(OC)=CC=3)=[N:12][C:11]=2[CH:34]([CH3:36])[CH3:35])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)C.Cl>CO>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:13]([CH2:23][OH:24])=[N:12][C:11]=2[CH:34]([CH3:36])[CH3:35])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 1.43 g of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1-(2-(2-pyridyl)ethyl)-1H-imidazole was added 20 ml of ethanol and 40 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 (ethyl acetate:methanol=10:1)to give 571 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-hydroxymethyl-1-(2-(2-pyridyl)ethyl)-1H-imidazole (112a)(yield 51%).

Workup

customAfter completion of the reaction
distillationthe solvent was distilled off under reduced pressure
additionan aqueous sodium hydrogen carbonate solution was added
extractionextracted with ethyl acetate
dry with materialThe extract was dried over sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record: ord-2d29c377ab0a474f8c9c0c8f54ef8837
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910506

Reaction notes

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