Reaktion #64016

Reaktionsgleichung

1-(4-chlorophenyl)-N-methyl-2-(1H-1,2,4-triazol-1-yl)ethanimine N-oxide

1-octadecene

→

3-(4-Chlorophenyl)-3-(1H-1,2,4-triazol-1-ylmethyl)-2-methyl-5-n-hexadecylisoxazolidine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis removed under reduced pressure
2. 2
   SonstigeThe residual dark solid is collected
3. 3
   Waschenwashed sequentially with acetonitrile and ether
4. 4
   SonstigeCrystallization from ethyl acetate
5. 5
   Sonstigegave 9.0 g (14%) of isomer A (3: R=4-Cl, n=15), melting at 100°-102° C.

Vorschrift

A solution of 32.8 g (0.131 mol) of 1-(4-chlorophenyl)-N-methyl-2-(1H-1,2,4-triazol-1-yl)ethanimine N-oxide (1: R=4-Cl) [prepared by reacting 2-(1H-1,2,4-triazol-1-yl)-4'-chloroacetophenone (35.38 g, 0.160 mol) with N-methylhydroxylamine hydrochloride (20.0 g, 0.240 mol) and NaHCO3 (20.12 g, 0.240 mol) in 500 ml ethanol] and 62.8 ml (0.196 mol) of 1-octadecene (2: n=15) in 400 ml toluene is refluxed for 48 hours under a nitrogen atmosphere. Upon cooling to room temperature the solvent is removed under reduced pressure. The residual dark solid is collected and washed sequentially with acetonitrile and ether. Crystallization from ethyl acetate gave 9.0 g (14%) of isomer A (3: R=4-Cl, n=15), melting at 100°-102° C.

Quelle