Triethylamine → 3-Phenyl-2-oxazolidinone
Reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[C:5]1([N:4]2[CH2:3][CH2:2][O:1][C:19]2=[O:21])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under N2, a solution of N-(2-hydroxyethyl)aniline (500 mg, 3.65 mmol) and triethylamine (1 mL, 7.29 mmol) in THF (2 mL) was added slowly to a solution of triphosgene (360 mg, 1.21 mmol) in THF (2 mL) at 0° C. The reaction mixture was stirred at 0° C. for one hour. The reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL) and extracted with methylene chloride (3×4 mL). The organic extracts were dried over sodium sulfate and concentrated. Silica gel chromatography (5%-35% EtOAc/CH2Cl2) gave 3-phenyl-1,3-oxazolidin-2-one. LCMS (ES) m/z 164.2 (M+H)+.
Workup
- customThe reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL)
- extractionextracted with methylene chloride (3×4 mL)
- dry with materialThe organic extracts were dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4f74a718c4b64641beb87ee30e96d635
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393873B2
Reaction notes
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