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

HRID 251906Notes

Reaction equation

HRID 251906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13](Cl)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1.C(#N)C.[NH2:23][C:24]1[C:32]([CH3:33])=[CH:31][C:30]([Cl:34])=[CH:29][C:25]=1[C:26](O)=[O:27].CS(Cl)(=O)=O>C(N(CC)CC)C>[Cl:34][C:30]1[CH:31]=[C:32]([CH3:33])[C:24]2[N:23]=[C:13]([C:12]3[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[N:9]=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=3)[O:14][C:26](=[O:27])[C:25]=2[CH:29]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 31297Methanesulfonyl chlorideHCID 116440442-Amino-5-chloro-3-methylbenzoic acidHCID 574582382-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

Product 1

HCID 668545686-chloro-2-[1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-oneYield 68.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

To a mixture of 1.0 g of 1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride and 10 ml of acetonitrile was added 0.60 g of 2-amino-5-chloro-3-methylbenzoic acid, and the resulting mixture was stirred at room temperature for 10 minutes. To the mixture, 0.46 ml of triethylamine was added. After the mixture was stirred at room temperature for 20 minutes, 0.92 ml of triethylamine was further added thereto. After the mixture was stirred at room temperature for 20 minutes, 0.28 ml of methanesulfonyl chloride was added thereto and the mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.98 g of 6-chloro-2-[1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-one of the formula:

Workup

  1. stirringAfter the mixture was stirred at room temperature for 20 minutes
  2. stirringAfter the mixture was stirred at room temperature for 20 minutes
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-928fe13506694362834062a488eff06b
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

Loading…