ChemicalBook CAS DataBase List 3-AMINO-2-OXAZOLIDINONE

3-AMINO-2-OXAZOLIDINONE synthesis

5synthesis methods

Product Name:3-AMINO-2-OXAZOLIDINONE
CAS Number:80-65-9
Molecular formula:C3H6N2O2
Molecular Weight:102.09

109-84-2

105-58-8

80-65-9

General procedure for the synthesis of 3-aminooxazolidin-2-one from 2-hydrazinoethanol and diethyl carbonate: 15.2 g (0.2 mol) of 2-hydrazinoethanol (Intermediate 1), 31.0 g (0.2 mol) of diethyl carbonate, and 3.0 g (57 mmol) of sodium methanol were added to a 100 mL three-necked flask, and the mixture was heated and refluxed for 4 hours. Upon completion of the reaction, the reaction mixture was cooled and a solid was precipitated. The solid was collected by vacuum filtration and dried. The solvent in the mother liquor was removed by distillation. The crude product was purified by column chromatography (eluent: methanol/dichloromethane, 1:20, v/v), and the resulting white solid was recrystallized in ethanol to give 15.3 g of 3-aminooxazolidin-2-one (Intermediate 2) in 75% yield. The product was characterized as follows: 1H-NMR (400 MHz, D2O) δ ppm: 4.33 (2H, t, J = 8.0 Hz), 3.94 (2H, s), 3.70 (2H, t, J = 4.0 Hz); EI-MS (m/z): 103.1 [M + H]+; Melting point: 64-66 °C.

109-84-2 Synthesis

109-84-2
309 suppliers
$6.00/5g

105-58-8
480 suppliers
$14.00/25g

80-65-9
126 suppliers
$60.00/10 mg

Yield:80-65-9 75%

Reaction Conditions:

with sodium methylate for 4 h;Reflux;

Steps:

[Preparation of Intermediate 2] 3-amino oxazolidinone
15.2g (0.2mol) 2-hydrazinoethanol (Intermediate 1), 31.0g (0.2mol) diethyl carbonate, and 3.0g (57mmol) sodium methoxide were added to a 100ml three-necked flask, and were refluxed for 4 hours, and after cooling, solids were precipitated, filtrated under vacuum, and dried. The solvent in the mother solution was removed by distillation. After column chromatography (eluent: methanol/dichloromethane (at a ratio of 1:20 by volume)), the obtained white solid and the dried solid were recrystallized in ethanol, to get 15.3g product (Intermediate 2), with a yield of 75%. ¹H-NMR(400MHz,D2O)δppm:4.33(2H,t,J=8.0Hz,J=8.0Hz),3.94(2H,s),3.70(2H,t,J= 4.0Hz,J=4.0Hz);EI-MS(m/z):103.1[M+H]+; m.p. 64-66°C.

References:

Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China;LI, Song;XIAO, Junhai;ZHAO, Mingming;ZHONG, Wu;WANG, Lili;ZHENG, Zhibing;XIE, Yunde;LI, Xingzhou;ZHAO, Guoming;ZHOU, Xinbo;WANG, Xiaokui;CHEN, Wei EP2952509, 2015, A1 Location in patent:Paragraph 0043; 0044

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497-25-6 Synthesis