5271-67-0Relevant articles and documents
Three step, one-pot process to prepare thiophene-2-carbonyl chloride (TCC), a key raw material in the manufacture of tioxazafen (Nemastrike)
Walker, Daniel P.,Graham, Charles R.,Miller, William H.,Koeller, Kevin J.
, p. 834 - 838 (2019)
Nematodes are parasitic organisms that cause significant damage to crops. Tioxazafen (Nemastrike), is a proprietary seed treatment being developed by Bayer AG as a broad-spectrum nematicide. Thiophene-2-carbonyl chloride (TCC) is the key raw material in the manufacture of tioxazafen. Current manufacturing routes to TCC suffer from byproduct formation and significant waste generation, which leads to high manufacturing cost. A potentially more cost-effective process for preparing TCC from commercial thiophene has been developed. The advantages of this new chemical approach are illustrated in the processing details described in this Letter.
Direct observation of fluorescent complex formation of acridinium-anilide-thiophene triad with poly-L-glutamic acid
Hu, Jingqiu,Joshi, Monica,Elioff, Michael
, p. 59 - 69 (2017)
Conformational changes and self-assembly process of polypeptides and proteins are important for biological processes. In order to investigate such changes, we prepared a fluorescent probe, thiophene-phenylanilide-acridinium triad, and investigated its pho
One-step Conversion of Amides and Esters to Acid Chlorides with PCl3
Li, Fangshao,Wu, Xiaofang,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing
supporting information, p. 4314 - 4317 (2021/07/16)
A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.
Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko
, p. 6504 - 6517 (2021/05/06)
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.
