Reaction #2254157

Reaction equation

8-Bromo-6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione

2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

pyridine

→

title compound

Yield 64.2%

8-bromo-6-chloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-benzo[d][1,3]oxazin-4-one

Yield 64.2%

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperatureheated to 100° C. for 4 h
3. 3
   workup.STIRRINGstirred for a further 16 h at room temperature
4. 4
   TemperatureThe reaction was then cooled in an ice-bath
5. 5
   Filtrationthe resulting white solid filtered
6. 6
   Washwashed with cold acetonitrile

Procedure

To a suspension of 8-Bromo-6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (5.0 g, 18.1 mmol) in acetonitrile (10 mL) was added a solution of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride (6.45 g, 20.8 mmol) in acetonitrile (8 mL). After stirring for 5 min pyridine (10.4 mL) was added dropwise. The reaction was stirred for a further 30 min at room temperature, then heated to 100° C. for 4 h and stirred for a further 16 h at room temperature. The reaction was then cooled in an ice-bath and the resulting white solid filtered and washed with cold acetonitrile to obtain the title compound (5.88 g, 64%).

Source