以2,2,3,3,4,4,5,5-八氟-1-戊醇(OFP)作为短碳氟链来源,三聚氯氰(TCT)为反应活性基团,通过一锅两步法合成了一种高活性的三嗪类缩合剂1-氯-3,5-双((八氟-1-戊基)氧基)-三嗪(DFCT),采用傅里叶变换红外光谱(FT-IR)、核磁共振(1H NMR、13C NMR、19F NMR)对目标产物(DFCT)进行了表征,通过质谱对中间体2,4-二氯-6-((八氟-1-戊基)氧基)-三嗪(DCFT)和目标产物DFCT进行了表征;同时对缩合试剂合成条件进行研究,确定了合成的较佳工艺:二氯甲烷为溶剂,氢氧化钠为中和试剂,n(TCT)∶n(OFP)=1∶2.2,先在0 ℃反应生成中间体DCFT,然后在30 ℃反应生成目标产物DFCT,收率为96%。用制备的DFCT作为缩合试剂,以羧酸和胺/醇为原料,分别合成了酰胺类目标产物(Ⅰa~Ⅰc)和酯类目标产物(Ⅱa~Ⅱc),说明DFCT可应用于酰胺化、酯化反应的缩合试剂,且反应条件温和,易于操作。
A triazine-type condensating agent with high activity, 1-chloro-3,5-bis((octafluoropentyl)oxy)-triazine(DFCT), was synthesized by one-pot two-step method, in which cyanuric chloride(TCT)was used as reactive group and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol(OFP)was used as the source of short fluorocarbon chain. The intermediate(2,4-dichloro-6-((octafluoropentyl)oxy)-triazine, DCFT)and the target product(DFCT)were characterized by FT-IR,1H NMR,13C NMR,19F NMR and mass spectrometry. The reaction conditions were optimized according to the yield of product: Dichloromethane was used as the solvent; sodium hydroxide was used as acid binding agent; n(TCT)∶n(OFP)=1∶2.2; the reaction temperature was 0 ℃ to generate DCFT, and then 30 ℃ to obtain the target product DFCT, and the yield of DFCT was 96%. DFCT was used as a condensating agent to activate carboxylic acid which would react with amines/alcohols to produce amides(Ⅰa-Ⅰc)/esters(Ⅱa-Ⅱc). It showed that DFCT could be used as a condensating agent for amidation and esterification reactions, and the reaction conditions were mild and easy to operate.