Hydrochloric Acid → [1-Benzyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl]methanol

HRID 1857702Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[C:11]([CH:22]([CH3:24])[CH3:23])[N:10]=[C:9]1[CH2:25][O:26]CC1C=CC(OC)=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]1[C:12]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[C:11]([CH:22]([CH3:24])[CH3:23])[N:10]=[C:9]1[CH2:25][OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 25 ml of methanol was dissolved 1.41 g (2.67 mmol) of 1-benzyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (17f), followed by addition of 12.5 ml of 6N-hydrochloric acid at room temperature with stirring, and the mixture was stirred under heating at 60° C. for 3 hour. This reaction mixture was concentrated under reduced pressure, the residual solution was neutralized with a saturated aqueous solution of sodium bicarbonate to be weakly basic, and was extracted with methylene chloride. The extract was rinced with water, and then, was dried over magnesium sulfate, arid the solvent was concentrated under reduced pressure. The residue was crystalized from n-hexane and collected by filtration to give 1.0 g (yield 92%) of [1-benzyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl]methanol (Compound I-16). mp 121-124° C.

Workup

stirringthe mixture was stirred
concentrationThis reaction mixture was concentrated under reduced pressure
extractionwas extracted with methylene chloride
dry with materialwas dried over magnesium sulfate
concentrationwas concentrated under reduced pressure
customThe residue was crystalized from n-hexane
filtrationcollected by filtration

Sources & evidence

ORD record: ord-854f426fe7264daeb356881e26134e23
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

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