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Names | |||
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Preferred IUPAC name 1,3-Oxazolidin-2-one | |||
Other names 1,3-Oxazolidin-2-one, 2-Oxo-1,3-oxazolidine, 2-Oxotetrahydro-1,3-oxazole | |||
Identifiers | |||
3D model (JSmol) | |||
ChemSpider | |||
ECHA InfoCard | 100.007.129 | ||
KEGG | |||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C3H5NO2 | |||
Molar mass | 87.077 g/mol | ||
Appearance | white or colorless solid | ||
Melting point | 86 to 89 °C (187 to 192 °F; 359 to 362 K) | ||
Boiling point | 220 °C (428 °F; 493 K) at 48 torr | ||
Related compounds | |||
Related compounds | Oxazolidine | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2-Oxazolidinone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring.
The compound arises by the reaction of an ethanolamine and dimethylcarbonate [1] or related phosgene equivalents. [2]
It is one of waste products generated in amine gas treating due to cyclization of ethanolamine carbamate. [3]
The compound was first reported in 1888 by German chemist Siegmund Gabriel. While investigating reactions of bromoethylamine hydrobromide, he treated it with silver carbonate and isolated a product with melting point around 90–91°C. He determined its empirical formula correctly, but neither gave it a specific name nor studied its properties. [4]
Nine years later Gabriel returned to the topic together with G. Eschenbach, developing a more efficient synthesis using sodium bicarbonate instead of the silver salt. They referred to the compound as "Oxäthylcarbaminsäureanhydrid" (hydroxyethylcarbamic acid anhydride), recognizing its relationship to ethanolamine and its cyclic structure. Their 1897 paper focused on optimizing the yield of oxazolidone and investigating some of its reactions, such as its conversion to 1-(2-hydroxyethyl)-3-phenylurea upon treatment with aniline. [5]
Oxazolidinones are useful as Evans auxiliaries, which are of interest for chiral synthesis. In a common implementation, an acid chloride substrate reacts with a chiral oxazolidinone to form an imide. Substituents at the 4 and 5 position of the oxazolidinone direct any aldol reaction to the alpha position of the carbonyl of the substrate. [6] Asymmetric Diels-Alder reactions are also enabled by these auxiliaries. [7]
Oxazolidinones are found in some antimicrobials. Oxazolidinones inhibit protein synthesis by interfering with the binding of N-formylmethionyl-tRNA to the ribosome. [8] (See Linezolid#Pharmacodynamics)
Some of the most important oxazolidinones are antibiotics. [9]
Examples of oxazolidinone-containing antibiotics:
A first commercially available 1,3-oxazolidinone is the antibiotic linezolid.
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