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- W2023722496 abstract "The formation of N,N-dimethylcarbamoyl chloride (DMCC) in Vilsmeier reactions (VRs) and the hydrolysis of DMCC during aqueous workup were investigated. The amount of DMCC formed was dependent on the chlorination reagent. The activity order was found to be: thionyl chloride > oxalyl chloride > phosphorus oxychloride. The concentrations of DMCC found in the tested reactions were normally at a level of 0−20 ppm. In the presence of a base the level was higher. DMCC hydrolyzed quickly under aqueous workup conditions. No more than 3 ppm of DMCC could be detected in the product after aqueous workup of the tested VR. Our results clearly indicate that by following the described procedure for VR it is perfectly safe from the health risk point of view to operate this chemistry when preparing compounds for pharmaceutical use. A very useful analytical procedure for detection and quantification of trace amounts of DMCC formed in the VR was developed. The method was based on derivatization of DMCC with ethanol to form ethyl N,N-dimethylcarbamate and analysis by GC coupled to a mass spectrometer in selected ion monitoring mode. The analytical method was selective and showed very good linearity. The limit of detection (LOD) and limit of quantification (LOQ) of DMCC using standard addition analysis with real Vilsmeier reaction matrices were determined to be LOD = 0.2 ppm and LOQ = 0.7 ppm." @default.
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- W2023722496 date "2009-07-02" @default.
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- W2023722496 title "Investigation on the Formation and Hydrolysis of <i>N</i>,<i>N</i>-Dimethylcarbamoyl Chloride (DMCC) in Vilsmeier Reactions Using GC/MS as the Analytical Detection Method" @default.
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