N-methyl-2-pyrrolidone → Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

HRID 394841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394841
[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5](Br)=[CH:6][CH:7]=1.CN1C(=O)CCC1.[CH3:22][S-:23].[Na+]>O>[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5]([S:23][CH3:22])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 13387N-methyl-2-pyrrolidoneHCID 4378561Sodium methanethiolateHCID 12100431HCID 12100431, Verbindung

Produkt 1

HCID 9860657Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

25 g (0.075 mol) of 3-(3,6-dibromo-2-methylphenyl)-4,5-dihydroisoxazole are initially charged in 12 mol of NMP. At a temperature of 100° C. and at a reduced pressure of 100 mbar, 29.3 g (0.09 mol) of a 21.5% strength methanolic solution of sodium thiomethoxide are added dropwise over a period of 40 min. The reaction mixture is stirred at 100° C. for 3 h and then stirred into 250 ml of water and extracted three times with 100 ml of toluene. The combined organic phases are washed once with 100 ml of water and then concentrated under reduced pressure. This gives 17.5 g of a dark oil. GC/MS shows, in addition to other isomers, 52.3% of the desired product. MSm/z: 287.

Aufarbeitung

  1. extractionextracted three times with 100 ml of toluene
  2. washThe combined organic phases are washed once with 100 ml of water
  3. concentrationconcentrated under reduced pressure
  4. additionGC/MS shows, in addition to other isomers, 52.3% of the desired product

Quellen und Nachweise

ORD-Eintrag
ord-f07d40b8823246318f792a9d120be48d
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06603017B2

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