Réaction #339084

Équation de réaction

triethylamine

1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride

2-amino-5-chloro-3-methylbenzoic acid

methanesulfonyl chloride

triethylamine

→

6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-one

Rendement 95.2%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 20 minutes
2. 2
   workup.STIRRINGAfter the mixture was stirred at room temperature for 20 minutes
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 3 hours
4. 4
   ConcentrationAfter the reaction mixture was concentrated under reduced pressure, ethyl acetate and water
5. 5
   workup.ADDITIONwere poured into the residue
6. 6
   Autreto separate layers
7. 7
   LavageThe organic layer was washed with water
8. 8
   Séchagedried over sodium sulfate
9. 9
   Concentrationconcentrated under reduced pressured

Mode opératoire

To a solution of 3.1 g of 1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride in 100 ml of acetonitrile, 1.9 g of 2-amino-5-chloro-3-methylbenzoic acid was added. The mixture was stirred at room temperature for 10 minutes and then, 1.0 g of triethylamine was added thereto. The mixture was stirred at room temperature for 20 minutes and then, 2.0 g of triethylamine was further added thereto. After the mixture was stirred at room temperature for 20 minutes, 1.2 g of methanesulfonyl chloride was added and the mixture was stirred at room temperature for 3 hours. After the reaction mixture was concentrated under reduced pressure, ethyl acetate and water were poured into the residue to separate layers. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressured. The resulting residue was subjected to silica gel column chromatography to obtain 4.2 g of 6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-one of the formula:

Source