Reaction #1578

Reaction equation

sodium hydroxide

4'-chloro-2'-fluoro-5'-[hexahydro-2,4,6-trioxo-3-(2-propynyl)-s-triazin-1-yl]acetanilide

hydrochloric acid

ethyl acetate

→

title product

Yield 82.2%

1-(5-Amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H, 3H, 5H)-trione

Yield 82.2%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureis refluxed for 3 hours
2. 2
   Otherthe phases are separated
3. 3
   WashThe organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine
4. 4
   Concentrationconcentrated in vacuo

Procedure

A mixture of 4'-chloro-2'-fluoro-5'-[hexahydro-2,4,6-trioxo-3-(2-propynyl)-s-triazin-1-yl]acetanilide (3.00 g, 8.5 mmol), and 3N hydrochloric acid (25 mL) in ethanol (50 mL) is refluxed for 3 hours, cooled to room temperature, and poured into ethyl acetate. 3N sodium hydroxide solution (25 mL) is added to the organic solution, and the phases are separated. The organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine, and concentrated in vacuo to give the title product as a beige solid (2.17 g, mp 118°-121° C.).

Source