Pyridine, 4-((5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-(2-(phenylmethoxy)ethyl)-1H-imidazol-1-yl)methyl)- → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-

HRID 1857758Notes

Reaction equation

C([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[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][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[C:11]([CH2:10][CH2:9][OH:8])=[N:15][C:14]=2[CH:16]([CH3:18])[CH3:17])[CH:21]=[C:22]([Cl:27])[CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In 12 ml of cocentrated hydrochloric acid was dissolved 2.3 g (4.5 mmol) of the benzyl compound (122b), and the mixture was heated at 100° C. for 4 hours. The mixture was neutralized with sodium hydrogen carbonate, and 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 (7% methanol/ethyl acetate) to give 1.28 g of 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-ylmethyl)-1H-imidazol-2-yl]ethanol (123b) as crystals (yield 67%). mp 121-122° C.

Workup

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 (7% methanol/ethyl acetate)

Sources & evidence

ORD record: ord-930a7d0a015847d195096d852802c1b3
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

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