Water → Metsulfuron

Participants

Reaction Steps

A solution of 0.5 g of potassium tert-butoxide and 1.0 g of methyl 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylbenzoate in 25 ml of dimethyl sulfoxide was stirred at ambient temperature for 3 hours. The yellow solution was then poured into 250 ml of cold water. The free carboxylic acid was precipitated by the addition of enough concentrated hydrochloric acid to reach pH 3. The crude product was filtered, washed with water and dried in vacuo. Recrystallization from acetonitrile yielded 0.5 g of the title compound, m.p. 157°-158° C. The mass spectrum of this compound exhibited the expected molecular ion at m/e=367. The infrared bands at 3300 cm-1 and 1725 cm-1 are consistent with the desired structure. The nuclear magnetic resonance spectrum showed peaks at 2.5 ppm (triazine CH3), 3.9 ppm (triazine OCH3) and 7.4-8.2 ppm (phenyl). The methyl ester peak present in the starting material was not observed in the spectrum of the product.

Provenance & Evidence