Imidazole-1-sulfonyl azide hydrochloride (1) is a white, slightly hygroscopic solid (mp 100–102 °C) that is soluble in water, acetonitrile, DMSO, DMF, and lower alcohols. It was reported by Goddard-Borger and Stick as a crystalline, shelf-stable, and easily prepared alternative to triflyl azide (TfN₃) in diazotransfer reactions.[1] It is widely used to prepare organic azides from aminosugars, aminoacids, and anilines because of its solubility in water. In addition, this reagent allows conversion of substrates with activated methylene groups into diazo compounds.[1] [2]

The preparation of imidazole-1-sulfonyl azide is conducted by a convenient two-step procedure (Scheme [1]).[1] First, sulfuryl chloride is reacted with NaN₃ to give ClSO₂N₃, which then reacts with imidazole. The crude base product is precipitated by ethanolic HCl.

To minimize explosion risks, a safer synthesis starting from sulfuryl diimidazole was developed (Scheme [2]).[3]

咪唑-1-磺酰基叠氮化物盐酸盐（1）是白色的，略有吸湿性的固体（熔点100-102°C），溶于水，乙腈，DMSO，DMF和低级醇。Goddard-Borger和Stick报道，在重氮转移反应中，它是结晶，易储藏，易于制备的三氟叠氮化物（TfN ₃）的替代物。[1] 由于它在水中的溶解度，它被广泛用于从氨基糖，氨基酸和苯胺制备有机叠氮化物。此外，该试剂还可以将带有活化亚甲基的底物转化为重氮化合物。[1] [2]

咪唑-1-磺酰基叠氮化物的制备通过方便的两步程序进行（方案[1]）。[1] 首先，使硫酰氯与NaN ₃反应，得到ClSO ₂ N ₃，然后使其与咪唑反应。粗制的基本产物通过乙醇盐酸沉淀。

为了最大程度地降低爆炸风险，开发了一种从硫基二咪唑开始的更安全的合成方法（方案[2]）。[3]