Reaction #2329054

Reaction equation

9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one

NaOH

→

title compound

Yield 87.0%

4-Bromo-2-(2H-[1,2,4]triazol-3-yl)-phenylamine

Yield 87.0%

Solvents

ethylene glycol

Conditions

Workup

1. 1
   TemperatureThe resulting solution was cooled to 27° C.
2. 2
   Otherto crystallize
3. 3
   workup.ADDITIONWater (146 mL) and 1-octanol (1.73 mL) were added
4. 4
   workup.ADDITIONthe pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL)
5. 5
   Filtrationthe solid was collected by filtration
6. 6
   Washwashed with water and 2-propanol
7. 7
   OtherDrying in vacuo

Procedure

To a well stirred slurry of 9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (32.0 g, 171 mmol) in ethylene glycol (146 mL) which was heated at 100° C., was added aqueous NaOH (32%, 22.4 ml, 241 mmol). The slurry was heated at 140° C. for 17.5 h. The resulting solution was cooled to 27° C. and the product began to crystallize. Water (146 mL) and 1-octanol (1.73 mL) were added and the pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL). The resulting slurry was stirred for 30 min, the solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (25.2 g, 87%) as a light yellow solid. MS: m/e=239.0/241.1 [M+H+].

Source