m-Chloroperbenzoic acid → 2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}-1-methyl-1H-imidazole

HRID 735347Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=O)C=1.[OH-:36].[Ca+2].[OH-:38]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)(=[O:38])=[O:36])[CH:12]=[CH:11]3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-{[6-(4-Fluorophenyl)-2-naphthyl]thio}-1-methyl-1H-imidazole (125 mg, 0.4 mmol) was dissolved in CH2Cl2 (1 mL) and was cooled to 0° C. 3-Chloroperbenzoic acid (224 mg, 1.0 mmol) was added and the solution stirred at ambient temperature for 1.5 h. The solution was diluted with CH2Cl2 (1 mL) and calcium hydroxide (277 mg, 0.6 mmol) was added. The suspension was stirred for 30 minutes before filtering through a pad of Hyflo; the liquors were evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 55% ethyl acetate/isohexane, to give the title compound as a white solid (67 mg). 1H NMR (500 MHz, d6-DMSO): δ 8.74 (1H, s), 8.36 (2H, m), 8.22 (1H, d, J=8.7 Hz), 8.04 (1H, d, J=8.6 Hz), 7.93-7.91 (3H, m), 7.50 (1H, s), 7.38 (2H, t, J=8.8 Hz), 7.12 (1H, s), 3.97 (3H, s); m/z (ES+) 367 [MH+].

Workup

additionwas added
stirringThe suspension was stirred for 30 minutes
filtrationbefore filtering through a pad of Hyflo
customthe liquors were evaporated in vacuo
customThe residue was purified by flash column chromatography on silica
washeluting with 55% ethyl acetate/isohexane

Sources & evidence

ORD record: ord-b7e28294f7cf4880a121c95fefcd75e3
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592456B2

Reaction notes

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