Methanol → Methyl 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoate

HRID 467932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467932
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(Cl)(Cl)=O.[CH3:32]O>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:32][O:19][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:23]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

Produkt 1

HCID 59563501Methyl 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (Example I5) (10 g) in toluene (150 ml) and dimethylformamide (0.1 ml) at ambient temperature was added dropwise thionyl chloride (3.5 ml). The reaction mixture was stirred at 50° C. for 2 hours. The solution was then cooled to 0° C. and methanol (2 ml) added slowly. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and aqueous sodium hydrogen carbonate (saturated) (50 ml) added to the residue. The mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried over sodium sulfate and concentrated to afford 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester as a yellow solid (11.5 g). 1H-NMR (CDCl3, 400 MHz): 7.95 (d, 1H), 7.55 (m, 4H), 7.45 (s, 1H), 4.10 (d, 1H), 3.90 (s, 3H), 3.70 (d, 1H), 2.60 (s, 3H) ppm.

Aufarbeitung

  1. customat ambient temperature
  2. temperatureThe solution was then cooled to 0° C.
  3. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  4. concentrationThe reaction mixture was concentrated
  5. additionaqueous sodium hydrogen carbonate (saturated) (50 ml) added to the residue
  6. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d3de05240e99441e92f785444499927a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623896B2

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