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

HRID 251906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 251906
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 668545686-chloro-2-[1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-oneAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

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:

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-928fe13506694362834062a488eff06b
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07867949B2

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