Butyl nitrite → 3-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

HRID 49665

Reaktionsgleichung

Reaktionsgleichung von HRID 49665
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:7]=2N)=[N:2]1.N(OCCCC)=O.[CH3:21][S:22]SC>[Cu]>[CH3:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:7]([S:22][CH3:21])[C:6]=1[C:3]1[CH2:4][CH2:5][O:1][N:2]=1

Komponenten

5

Edukt 3

HCID 10996Butyl nitriteHCID 12232Dimethyl DisulfideHCID 97940062-(4,5-Dihydroisoxazol-3-yl)-3-methylaniline

Produkt 1

HCID 108783423-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

40 g (0.22 mol) of 2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline and 1.5 g of copper powder are initially charged in 300 ml of dimethyl disulfide, and 26.1 g of n-butyl nitrite (0.23 mol) are added dropwise at 55-66° C. The mixture is then stirred at 60° C. for 1.5 hours. For work-up, the hot mixture is filtered through activated carbon and then washed with dilute hydrochloric acid and water and then concentrated under reduced pressure. This gives 44.5 g (88%) of a dark oil which solidifies after a while (content according to HPLC (95%). The product can be purified further by trituration with methyl tert-butyl ether.

Aufarbeitung

  1. filtrationFor work-up, the hot mixture is filtered through activated carbon
  2. washwashed with dilute hydrochloric acid and water
  3. concentrationconcentrated under reduced pressure
  4. customThe product can be purified further by trituration with methyl tert-butyl ether

Quellen und Nachweise

ORD-Eintrag
ord-10d7ee252c7444df9fec62dd0a3dc293
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706886B2

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