Réaction #50520

Équation de réaction

sodium hydroxide

propargylamine

methyl trifluoromethanesulfonate

p-trifluoromethylbenzonitrile

→

1,5-dimethyl-2-(4-trifluoromethylphenyl)imidazole

Solvants

methylene chloride

acetonitrile

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurecooled to 5° C
2. 2
   Températurecooled to 5° C.
3. 3
   AutreThe organic layer was separated
4. 4
   Autrethe solvent evaporated under reduced pressure, and 50 ml of toluene
5. 5
   workup.ADDITIONadded
6. 6
   TempératureThe mixture was refluxed for 3 hours
7. 7
   Températurecooled
8. 8
   Autrethe solvent evaporated under reduced pressure
9. 9
   Autrethe residue recrystallized from isopropyl ether

Mode opératoire

A mixture of methyl trifluoromethanesulfonate (3.3 ml) and p-trifluoromethylbenzonitrile (5.17 g) was heated at 65° C. for 31/2 hours, then cooled to 5° C. The mixture was then dissolved in 10 ml of acetonitrile, and 2 ml of propargylamine in 10 ml of acetonitrile was added. The mixture was stirred at room temperature for 16 hours, then cooled to 5° C. and 3 ml of concentrated sodium hydroxide added (about 1 equivalent), followed by 40 ml of methylene chloride. The organic layer was separated, the solvent evaporated under reduced pressure, and 50 ml of toluene added. The mixture was refluxed for 3 hours, cooled, the solvent evaporated under reduced pressure, and the residue recrystallized from isopropyl ether, to yield 4.6 g of 1,5-dimethyl-2-(4-trifluoromethylphenyl)imidazole, a compound of Formula (6), m.p. 130° C.

Source