m-Chloroperbenzoic acid → HCID 86702132, compound

HRID 1776183Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH2:12][C:13]([CH3:15])=[CH2:14])[S:8]([CH3:11])(=[O:10])=[O:9].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH2:12][C:13]1([CH3:15])[CH2:14][O:24]1)[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirring solution of N-(furan-2-ylmethyl)-N-(2-methylallyl)methanesulfonamide (1.0 g, 4.3 mmol) in anhydrous methylene chloride (20 mL) was added 3-chloroperbenzoic acid (70%, 2.1 g, 8.6 mmol). The mixture was stirred at ambient temperature for 2 hours and at 40° C. for 18 hours. The mixture was diluted with methylene chloride and successively washed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions. The organic layer was dried (anhydrous sodium sulfate), filtered, and concentrated. The crude residue was purified by silica gel column chromatography (10-60% ethyl acetate in hexanes) to give a clear oil (0.278 g, 26%). 1H NMR (CDCl3, 300 MHz) δ 7.40-7.35 (dd, 1H, J=0.9, 1.8 Hz), 6.33-6.30 (m, 2H), 4.52-4.51 (m, 2H), 3.48-3.43 (d, 1H, J=15 Hz), 3.13-3.09 (d, 1H, J=15 Hz), 2.73-2.72 (d, 1H, J=4.5 Hz), 2.70 (s, 3H), 2.62-2.61 (d, 1H, J=4.5 Hz), 1.35 (s, 3H).

Workup

washsuccessively washed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions
dry with materialThe organic layer was dried (anhydrous sodium sulfate)
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by silica gel column chromatography (10-60% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-00784c6cbd404a48952a727b3cb675a1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265772B2

Reaction notes

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