151331-80-5Relevant articles and documents
Intramolecular and bimolecular nucleophilic substitutions of rimsulfuron sulfonylurea
Rouchaud, J.,Neus, O.,Moulard, C.
, p. 59 - 66 (2007/10/03)
The sulfonylurea herbicide rimsulfuron 1 (N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamide) in aqueous solutions of KOH, NaOH, NH4OH, or dilute HCl, and thermally (rimsulfuron or monomethylated rimsulfuron at the sulfonamide hydrogen) was transformed by SO2 extrusion and intramolecular nucleophilic substitution into 2-(N-(4,6-dimethoxy)pyrimidin-2-yl)amino-3-ethylsulfonylpyridine 3.In mild methanol + HCl conditions, the intermediate rearranged urea N-(4,6-dimethoxypyrimidin-2-yl)-N-(3-(ethylsulfonyl)-2-pyridinyl)urea 2 was isolated.In concentrated hydrochloric acid, rimsulfuron 1 was transformed by bimolecular nucleophilic substitution successively into 2-chloro-3-ethylsulfonylpyridine 6 and 2-hydroxy-3-ethylsulfonylpyridine 4.Sodium sulfite transformed rimsulfuron 1 into a mixture of 2-sodiumsulfonate-3-ethylsulfonylpyridine 7 and amine 3.