Oxolamine synthesis
- Product Name:Oxolamine
- CAS Number:959-14-8
- Molecular formula:C14H19N3O
- Molecular Weight:245.32
Yield: 84%
Reaction Conditions:
Stage #1:5-(2-Chloroethyl)-3-phenyl-1,2,4-oxadiazole with potassium iodide in acetonitrile at 20; for 0.5 h;
Stage #2:diethyl amine hydrochloride with potassium carbonate in acetonitrile for 2.5 h;Reflux;
Steps:
Oxolamine (7)
A mixture of benzamidoxime (1.47 mmol), 3-chloropropanoic anhydride (1.77 mmol) and HClO4-SiO2 (5 mol%) was stirred at 80 °C for 8 min. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature, diluted with dichloromethane (5 mL) and the catalyst was allowed to settle down. Then the reaction mixture was filtered, washed with dichloromethane (5 mL), and the combined organic layers were washed with saturated aq. NaHCO3 and water. The obtained organic layer was dried over anhy. Na2SO4 and concentrated under reduced pressure to get crude compound. The crude was then purified by column chromatography on silica gel using hexane/EtOAc (8:2) as eluents to get pure compound 6. Then, a mixture of compound-6 (1.05 mmol) and KI (1.05 mmol) in CH3CN was stirred at room temperature for 30 min. To the reaction mixture, K2CO3 (2.64 mmol) and Et2NH.HCl (1.58 mmol) were added and reaction was stirred under reflux conditions for 2.5 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature, water was added and extracted with ethyl acetate. The organic layer was dried over anhy. Na2SO4 and concentrated under reduced pressure to get crude. The crude was purified by using column chromatography on silica gel using hexane/EtOAc (7:3) as eluents to afford pure oxolamine as brown colour liquid.
References:
Tadikonda, Ramu;Nakka, Mangarao;Gajula, Mahaboob Basha;Rayavarapu, Srinuvasarao;Gollamudi, Padma Rao;Vidavalur, Siddaiah [Synthetic Communications,2014,vol. 44,# 13,p. 1978 - 1986] Location in patent:supporting information
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