Diisopropylethylamine → HCID 22347194, compound
Reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([NH:6][CH2:7][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:6]2[CH2:7][CH:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:9][C:28]2=[O:30])=[CH:16][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution containing 2-(4-bromoanilino)-1-phenyl-1-ethanol (0.74 g, 0.00253 mol), N,N-diisopropylethylamine (1.01 g, 0.00786 mol) and N,N-dimethylaminopyridine (0.092 g, 0.00076 mol) in anhydrous dichloromethane (32 mL) was cooled to 0° C. and a solution of triphosgene (0.38 g, 0.00127 mol) in anhydrous dichloromethane (8 mL) was added dropwise. The reaction mixture was slowly warmed up to ambient temperature while stirring under an atmosphere of nitrogen for eighteen hours. The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 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 3-(4-bromophenyl)-5-phenyl-1,3-oxazolan-2-one (0.62 g, 0.00192 mol) as a white solid.
Workup
- temperatureThe reaction mixture was slowly warmed up to ambient temperature
- washThe organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 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-9524202428154aa3960467a2d3ef9734
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06660744B1
Reaction notes
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