Methanol → HCID 18463536, compound

HRID 2231104Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:14][C:13]([C:15]([F:18])([F:17])[F:16])=[N:12][C:11]=2[C:19]2[CH:24]=[CH:23][C:22](SC)=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].O[O:28][S:29]([O-:31])=O.[K+].[CH3:33]O>O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[N:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[NH:12][C:11]=2[C:19]2[CH:24]=[CH:23][C:22]([S:29]([CH3:33])(=[O:31])=[O:28])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(3-Fluoro-4-methoxyphenyl)-5-[4-(methylthio)phenyl]-2-(trifluoromethyl)-1H-imidazole (516 mg, 1.35 mmol) from step 4 was dissolved in methanol (10 ml) and cooled to 0° C. OXONE® (2.46 g, 4 mmol) in water (10 ml) was added. After the addition, the ice bath was removed and the reaction was stirred at ambient temperature for 3 hours. The mixture was extracted with chloroform (3×50 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography, affording 4-(3-fluoro-4-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)-1H-imidazole as a solid (98 mg): m.p. 228-234° C. (DSC) The structure assignment was supported by NMR. Mass spectrum (EI, m/e): 414. Anal. Calc'd. for C18H14N2F4O3S: C, 52.17; H, 3.41; N, 6.76. Found: C, 52.30; H, 3.62; N, 6.53.

Workup

additionAfter the addition
customthe ice bath was removed
extractionThe mixture was extracted with chloroform (3×50 ml)
dry with materialThe combined organic phases were dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-856a9dfabd2e4b3ca7e137102e5337d8
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06426360B1

Reaction notes

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