1H-Imidazole, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-2-(2-(phenylmethoxy)ethyl)- → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-

HRID 1857756Notes

Reaction equation

C([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:28][CH3:29])[C:13]([S:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>Cl>[Cl:26][C:24]1[CH:25]=[C:20]([S:19][C:13]2[N:12]([CH2:28][CH3:29])[C:11]([CH2:10][CH2:9][OH:8])=[N:15][C:14]=2[CH:16]([CH3:17])[CH3:18])[CH:21]=[C:22]([Cl:27])[CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In 16 ml of cocentrated hydrochloric acid was dissolved 3.8 g (8.5 mmol) of the benzyl compound (122a), and the mixture was heated at 100° C. for 2 hours. After cooling, the mixture was neutralized with sodium hydrogen carbonate, extracted with ethyl acetate, the extract was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1% methanol:ethyl acetate), washed with n-hexane, and filtered to give 2.57 g of 2-[5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl]ethanol (123a) as crystals (yield 85%). mp 80-81° C.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washthe extract was washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (1% methanol:ethyl acetate)
washwashed with n-hexane
filtrationfiltered

Sources & evidence

ORD record: ord-9cdd68e11446406b8abf7246844413a2
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

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