Dimethylthiocarbamoyl chloride is an organosulfur compound with the formula (CH3)2NC(S)Cl. A yellow solid, it is often encountered as a yellow syrup. It is a key reagent in the synthesis of arylthiols via the Newman-Kwart rearrangement.
Synthesis and reactions Representative of other thiocarbamoyl chlorides, dimethylthiocarbamoyl chloride is electrophilic, serving as a source of R2NC(S)+.R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). It is analogous to dimethylcarbamoyl chloride (R2NC(O)Cl).
Dimethylthiocarbamoyl chloride is prepared by chlorination of the related tetramethylthiuram disulfide: [Me2NC(S)]2S2 + 3 Cl2 → 2 Me2NC(S)Cl + 2 SCl2
Dimethylthiocarbamoyl chloride reacts with dithiocarbamates (R2NCS) to give thiuram sulfides [R2NC(S)]2S. With methanethiolate, it gives methyl dimethyldithiocarbamate (Me2NC(S)SMe).
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