Diisopropylethylamine → 5-Benzyl-3-(4-bromophenyl)-1,3-oxazolan-2-one

HRID 897627

Reaction equation

[Br:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][CH2:7][CH:8]([OH:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH2:9]([CH:8]1[O:16][C:29](=[O:31])[N:6]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:18][CH:17]=2)[CH2:7]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution containing 1-(4-bromoanilino)-3-phenyl-2-propanol (1.90 g, 0.00621 mol), N,N-diisopropylethylamine (2.48 g, 0.0193 mol) and N,N-dimethylaminopyridine (0.152 g, 0.00124 mol) in anhydrous dichloromethane (64 mL) was cooled to 0° C. and the solution of triphosgene (0.92 g, 0.0031 mol) in anhydrous dichloromethane (16 mL) was added dropwise. The reaction mixture was slowly warmed up to ambient temperature while stirring under an atmosphere of nitrogen for 18 hours. The organic phase was washed with saturated solution of sodium bicarbonate in water (70 mL), brine (60 mL) and dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield 5-benzyl-3-(4-bromophenyl)-1,3-oxazolan-2-one (1.25 g, 0.00377 mol) as a white solid.

Workup

temperatureThe reaction mixture was slowly warmed up to ambient temperature
washThe organic phase was washed with saturated solution of sodium bicarbonate in water (70 mL), brine (60 mL)
dry with materialdried with magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue purified by flash chromatography on silica

Sources & evidence

ORD record: ord-02b8f9dae8824ecb9b9fa269f4090091
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921763B2

Linked notes

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