Chlorodifluoromethane → 2-Chloro-4-fluoro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-benzoic Acid Methylester

HRID 2120082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120082
Cl[CH:2]([F:4])[F:3].[CH3:5][O:6][C:7](=[O:23])[C:8]1[CH:13]=[C:12]([N:14]2[C:18](=[O:19])[NH:17][C:16]([CH3:20])=[N:15]2)[C:11]([F:21])=[CH:10][C:9]=1[Cl:22].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:5][O:6][C:7](=[O:23])[C:8]1[CH:13]=[C:12]([N:14]2[C:18](=[O:19])[N:17]([CH:2]([F:4])[F:3])[C:16]([CH3:20])=[N:15]2)[C:11]([F:21])=[CH:10][C:9]=1[Cl:22]

Komponenten

6

Edukt 3

HCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 136352415HCID 136352415, Verbindung

Produkt 1

HCID 120971882-Chloro-4-fluoro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-benzoic Acid MethylesterAusbeute 109 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

An excess of chlorodifluoromethane (97 g) was bubbled into a mixture of triazolinone from step 2 (7.04 g, 24.6 mmol), tetrabutylammonium bromide (9.67 g, 30.0 mmol), potassium carbonate (16.6 g, 122 mmol) and dimethylformamide (200 ml) in such a way that T<36° C. over a period of 30 minutes. The mixture was cooled and filtered. The filtrate was concentrated under reduced pressure and the residue partitioned between water and methylene chloride. The organic layer was washed with water, dried and concentrated under reduced pressure to give a dark oil (9.00 g), which was chromatographed on silica gel (eluent: ethyl acetate/hexane) to give the title compound. Yield: 1.48 g (17.9%).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue partitioned between water and methylene chloride
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e40463f53a548a9957613493408b85a
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06689773B2

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