2-(Chloromethyl)-2-methyloxirane → N-{2-[(2-Methyl-2-oxiranyl)methoxy]phenyl}benzamide

HRID 490320Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[CH2:18][C:19]1([CH3:22])[CH2:21][O:20]1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:18][C:19]1([CH2:22][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:21][O:20]1

Participants

Conditions

Temperature: 72.5 °C

Procedure

A mixture of N-(2-hydroxyphenyl)benzamide (159 mg; 0.75 mmol), 2-(chloromethyl)-2-methyloxirane (1.60 g, 15 mmol), and benzyltriethylammonium chloride (27 mg, 0.12 mmol) was stirred at 70-75° C. for 6 h After cooling to room temperature, water (2 ml) was added and the mixture was vigorously shaken. It was extracted with dichloromethane (2×5 ml), and the combined organic extracts were washed with aq. NaOH (2M, 5 ml) and water (10 ml). Drying with Na2SO4, evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 25 to 50%) afforded title compound as yellowish solid (131 mg, 0.46 mmol, 62%).

Workup

temperatureAfter cooling to room temperature
stirringthe mixture was vigorously shaken
extractionIt was extracted with dichloromethane (2×5 ml)
washthe combined organic extracts were washed with aq. NaOH (2M, 5 ml) and water (10 ml)
dry with materialDrying with Na2SO4, evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 25 to 50%)

Sources & evidence

ORD record: ord-01f20dd210404f21ad8a5be1ea66f589
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528156B2

Reaction notes

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