Hydrochloric Acid → Pyroxsulam

Participants

Reaction Steps

2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidine (9.8 g, 0.050 mol) and N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-S,S-dimethyl-sulfilimine hydrochloride salt (1.5 g, 0.005 mol) solids were combined with 2-methoxy-4-(trifluoromethyl)-pyridine-3-sulfonyl chloride (14 g, 0.051 mol) in acetonitrile (40 mL). 3,5-Lutidine (31 g, 93% technical) was added, and the mixture was stirred at room temperature for 22 hours. The mixture was warmed to 42° C. and treated with 3 N HCl (65 mL), after which the mixture was allowed to cool to room temperature over 1.5 hours. The solids were collected by filtration, washed with a 2:1 v/v solution of water:acetonitrile (20 mL), and dried under vacuum at 60° C. to afford 18 g of product assaying at 94 wt % (78% yield).

Provenance & Evidence