Development of a Pilot-Plant-Scale Synthesis of an Alkylated Dihydrobenzothiadiazole S, S-Dioxide: Incorporation of a Late-Stage Mitsunobu Reaction†

…, W Auguscinski, P Fung, R Galante, W Liu…

Index: Connolly, Terrence J.; Auguscinski, Waldemar; Fung, Peter; Galante, Rocco; Liu, Weiguo; McGovern, Linda; Sebastian, Alice; Shen, Xiaole; Shi, Xinxu; Wilk, Boguslawa; Varsalona, Richard; Zhong, Huijuan Organic Process Research and Development, 2010 , vol. 14, # 4 p. 868 - 877

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Citation Number: 5

Abstract

The process used to prepare a functionalized dihydrobenzothiadiazole S, S-dioxide on a pilot plant scale is described. Key changes to the original synthesis included: modifying SNAr reaction conditions between a substituted aniline and 2-fluoronitrobenzene from n- BuLi/− 78° C to KO t Am/0 to 15° C; replacement of a NaIO4− RuCl3 oxidizing system with bleach under phase transfer conditions; and a late-stage Mitsunobu reaction. The ...