Réaction #64016

Équation de réaction

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

Solvants

toluene

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source