| Identification | Back Directory | [Name]
(S)-5-ChloroMethyl-2-oxazolidinone | [CAS]
169048-83-3 | [Synonyms]
(S)-5-ChloroMethyl-2-oxazolidinone
(S)-5-(ChloroMethyl)oxazolidin-2-one
2-Oxazolidinone, 5-(chloromethyl)-, (5S)-
(5S)-5-(Chloromethyl)-1,3-oxazolidin-2-one | [Molecular Formula]
C4H6ClNO2 | [MDL Number]
MFCD08706410 | [MOL File]
169048-83-3.mol | [Molecular Weight]
135.55 |
| Chemical Properties | Back Directory | [Melting point ]
86℃ | [Boiling point ]
382.8±11.0 °C(Predicted) | [density ]
1.294±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
12.09±0.40(Predicted) | [Appearance]
White to off-white Solid | [Optical Rotation]
15.2° (C=1.00 g/100ml, DCM) |
| Hazard Information | Back Directory | [Synthesis]
Potassium cyanate (4.38 g, 53.5 mmol) was dissolved in 220 mL of water and (S)-(+)-epichlorohydrin (2.50 g, 27.0 mmol) was added slowly. The reaction mixture was stirred under reflux conditions for 15 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (5 x 200 mL) while it was still moderately warm. All organic phases were combined, dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure to afford (S)-5-chloromethyl-2-oxazolidinone, initially as a wax, which was converted to an off-white solid (2.18 g, 60% yield) after drying overnight under vacuum. | [References]
[1] European Journal of Organic Chemistry, 2001, # 13, p. 2425 - 2433
[2] Patent: WO2008/156718, 2008, A1. Location in patent: Page/Page column 25-26
[3] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 3, p. 258 - 262
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2597 - 2600
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 2, p. 892 - 905 |
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