2,5-二取代1,3,4-噻二唑的合成

Sythesis of 2,5-disubstitute-1,3,4-thiadiazole

以5-氨基-2-巯基-1,3,4-噻二唑为原料,经过氨基酰基化、氯气氧化制得5-乙酰胺基-1,3,4-噻二唑-2-磺酰氯,该化合物与N-甲基哌嗪、苯胺反应,合成两个未见报道的目标产物:5-乙酰胺基-1,3,4-噻二唑-2-(N-甲基哌嗪磺酰胺)和5-乙酰胺基-1,3,4-噻二唑-2-(磺酰苯胺)。结果表明:原料酰基化的最佳条件为:物料的物质的量之比n(噻二唑)∶n(乙酸酐)=1∶1.25,反应温度为70℃,冰醋酸12 mL条件下,薄层色谱点板跟踪反应进程,目标产物収率为88%以上;目标化合物的最佳条件为:乙醇作溶剂,物料比1∶2,薄层色谱点板跟踪反应进程,室温条件下目标产物收率在88%以上,产品纯度均在97%以上。并利用IR1、H-NMR、LC-MS对目标产物进行表征。

5-acetylamino-1,3,4-thiadiazole-2-sulfonyl chloride compound was synthesized using 5-amino-2-mercapto-1,3,4-thiadiazole which was acidylated and oxidized with gaseous chlorine.By its reaction with N-methyl piperazine and aniline,two new target produces were obtained as 5-acetylamino-1,3,4-thiadiazole-(2-N-methyl piperazine) sulfonylanilin and 5-acetylamino-1,3,4-thiadiazole-(2-sulfonyl)-aniline.The results showed that the best acidylation conditions for raw materials were as follows: the proportion of 5-ami...