双标记~(13)C,~(15)N_3-呋喃妥因的制备

以双标记13 C,15 N3-氨基脲为原料,先与苯甲醛缩合,继而与氯乙酸乙酯取代、环化,再经盐酸水解反应后与5-硝基糠醛二乙酯反应,最终制得双标记13 C,15 N3-呋喃妥因.产物经红外光谱、高效液相色谱及质谱表征.结果表明,所选用的合成路线反应条件温和,产物总收率高于60%,且同位素丰度不下降;目标产物的化学纯度>99.0%,13 C同位素丰度>98%,15 N同位素丰度>99%.

Preparation of double labeled 13C, 15N3-nitrofurantoin

A novel method was established to synthesize double labeled 13C,15N3-nitrofurantoin.Starting material 13C,15N3-semicarbazide was firstly converted to benzaldehyde semicarbazone（II） by condensation with benzaldehyde.Compound（II） was then allowed to react with ethyl α-chloroacetate in the presence of sodium ethoxide,forming 1-benzylideneaminohydratoin（Ⅲ）.Compound（Ⅲ） was hydrolyzed with hydrochloric acid and condensed with 5-nitro furfural diacetate,generating the target compound,nitrofurantoin-（13C,15N3）（V）.As-synthesized target product was characterized by infrared spectrometry,high-performance liquid chromatography,and mass spectrometry.It has been found that the established synthetic route is dominated by mild reaction conditions and gives rise to the final product in a yield of above 60%,while the abundance of the isotopes does not tend to decline.Namely,the chemical purity of the target product is above 99.0%,and the abundances of 13C and 15N are above 98% and 99%,respectively.