Hydrochloric Acid → HCID 67033435, compound
Reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH2:3][OH:4].Cl.[OH-].[K+].[C:14](=O)(OC(Cl)(Cl)Cl)[O:15]C(Cl)(Cl)Cl>O.C1COCC1>[N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:2]1[CH2:3][O:4][C:14](=[O:15])[NH:1]1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-amino-2-(pyridin-2-yl)ethanol (3.8 g, 28 mmol) (as the bis HCl salt) in water (50 mL) cooled to 0° C. was added potassium hydroxide (11 g, 19 mmol) followed by THF (50 mL) and the reaction stirred for 20 minutes at 0° C., followed by addition of bis(trichloromethyl) carbonate (8.2 g, 28 mmol) as the solid and stirring at 0° C. for 2 hours. The reaction was next poured into water and extracted with EtOAc and the combined organic layers were washed with 1N NaOH, brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by normal phase chromatography using EtOAc as eluent to yield 4-(pyridin-2-yl)oxazolidin-2-one (1.4 g, 8.5 mmol, 31% yield).
Workup
- stirringstirring at 0° C. for 2 hours
- extractionextracted with EtOAc
- washthe combined organic layers were washed with 1N NaOH, brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude material was purified by normal phase chromatography
Sources & evidence
- ORD record
- ord-5ba09d245b4c4ecabc7d33336fde4a28
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865726B2
Reaction notes
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