Water → Fenoxanil

Participants

Reaction Conditions

Reaction Steps

A stirred solution of (R)-2-(2,4-dichlorophenoxy)propionyl chloride (380.25 g, 1.5 mol) in toluene is cooled to -10° C. and treated simultaneously, with cooling, with 2-amino-2,3-dimethylbutyronitrile (168.3 g, 1.5 mol) and triethylamine (181.8 g, 1.8 mol) so as to maintain a reaction temperature range of -5° C. to -10° C. When the simultaneous addition of amines is complete, the reaction mixture is stirred at -5° C. for 2 hours, allowed to warm to room temperature in the absence of external heating, and treated with water. The phases are separated. The organic phase is cooled to 0° C., treated with 10% NaOH, and stirred for 1 hour at 0° C. The phases are separated. The organic phase is again washed with fresh 10% NaOH for 1 hour at 0° C., separated and washed a third time at 0° C. for 1 hour with fresh 10% NaOH. The organic phase is then washed sequentially with water, brine and water, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is crystallized in petroleum ether to give the title product as a white solid, 435 g (88% yield) identified by NMR analysis.

Provenance & Evidence