Sulfuryl Chloride

Maynard, George D.

doi:10.1002/047084289x.rs140

Cited by 3 publications

(3 citation statements)

References 70 publications

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“…Phosgene and chloropicrin were chosen, as they have been used as CWAs in the past and are known for their high toxicity and their potential for chlorination . Oxalyl chloride, thionyl chloride, and sulfuryl chloride completed our sample set as these are widely used in industrial processes as chlorinating agents. − …”

Section: Introductionmentioning

confidence: 99%

Influence of Chlorinating Agents on the Formation of Stable Biomarkers in Hair for the Retrospective Verification of Exposure

et al. 2022

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Chlorine, as a dual-use chemical, is an essential industrial chemical which has been used as a chemical weapon in the past due to its toxicity and availability. The retrospective verification of chlorine intoxication is often especially challenging, and unambiguous markers are still missing. In this study, the effects of different chlorinating and oxidizing agents on human hair were investigated. Samples were exposed to a variety of chlorinating chemicals for a short time and then completely hydrolyzed by a HBr solution to break down their keratin proteins into individual amino acids. After derivatization and targeted liquid chromatography-mass spectrometry analysis, 3-chlorotyrosine and 3,5dichlorotyrosine were unambiguously identified from human hair exposed to chlorine, hypochlorite, and sulfuryl chloride. Our results show long-term stability of these markers in the biological matrix, as the chlorotyrosines can still be found 10 months post-exposure at the same levels. Finally, an untargeted analysis was able to discriminate between some of the different intoxicants.

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Section: Introductionmentioning

confidence: 99%

Influence of Chlorinating Agents on the Formation of Stable Biomarkers in Hair for the Retrospective Verification of Exposure

et al. 2022

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“…(4) Fast mixing and rapid heat removal in a continuous process would likely allow the reaction temperature to be raised, avoiding the cryogenic (−20 °C) conditions employed for the batch reaction, thereby saving infrastructure and energy costs. (5) The hazardous and reactive nature of both the Grignard reagent and sulfuryl chloride could be controlled through the use of a fully enclosed flow system, compared with a batch process, where open handling could occur.…”

Section: Introductionmentioning

confidence: 99%

A Practical and Robust Multistep Continuous Process for Manufacturing 5-Bromo-N-(tert-butyl)pyridine-3-sulfonamide

Strotman

Savage

et al. 2019

Org. Process Res. Dev.

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A multistep continuous flow process involving (1) magnesium−halogen exchange, (2) sulfonylation with sulfuryl chloride, and (3) reaction with tertbutylamine was developed for the synthesis of an arylsulfonamide pharmaceutical intermediate in the synthesis of BMS-919373. The process was successfully implemented, including a robust control strategy to manage the levels of several process impurities, to produce 76 kg of 5-bromo-N-(tert-butyl)pyridine-3-sulfonamide (2). As the instability of the reactive intermediates and existence of strong exotherms made a batch process unsuitable for production beyond a 1 kg scale, the alternative continuous process led to a practical and robust manufacturing route to the active pharmaceutical ingredient.

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“…In addition to the desired product 3 , varying levels of two impurities were observed from the sulfonylation step after the reaction was quenched with ammonium hydroxide (Table ). These impurities were identified as chlorinated arene 9 and sulfinic acid 10 , suggesting the presence of sulfuryl chloride, a well-known chlorinating reagent, − in the batch of chlorosulfonic acid employed. Consistent with this hypothesis, the amounts of these impurities were found to depend on the batch of chlorosulfonic acid used (entries 1 and 2), and a significant increase in the quantity of both was observed upon the addition of one equivalent of sulfuryl chloride to the chlorosulfonic acid (entry 3).…”

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confidence: 99%

Development of a Green and Sustainable Manufacturing Process for Gefapixant Citrate (MK-7264). Part 5: Completion of the API Free Base via a Direct Chlorosulfonylation Process

Maso

Ren

Zhang

et al. 2020

Org. Process Res. Dev.

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A scalable two-pot sulfonamidation through the process has been developed for the synthesis of gefapixant citrate, a P2X3 receptor antagonist that is under investigation for the treatment of refractory and unexplained chronic cough. Direct conversion of the diaryl ether precursor to a sulfonyl chloride intermediate using chlorosulfonic acid, followed by treatment with aqueous ammonia hydroxide, provided the desired sulfonamide in high yield. A pH-swing crystallization allowed for the formation of a transient acetonitrile solvate that enables the rejection of two impurities. After drying, the desired anhydrous free base form was isolated in high yield and purity.

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Sulfuryl Chloride

Cited by 3 publications

References 70 publications

Influence of Chlorinating Agents on the Formation of Stable Biomarkers in Hair for the Retrospective Verification of Exposure

Influence of Chlorinating Agents on the Formation of Stable Biomarkers in Hair for the Retrospective Verification of Exposure

A Practical and Robust Multistep Continuous Process for Manufacturing 5-Bromo-N-(tert-butyl)pyridine-3-sulfonamide

Development of a Green and Sustainable Manufacturing Process for Gefapixant Citrate (MK-7264). Part 5: Completion of the API Free Base via a Direct Chlorosulfonylation Process

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