Reaction equation
F[C:2](F)(F)S(OC)(=O)=O.[F:10][C:11]([F:21])([F:20])[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[CH2:22]([NH2:25])[C:23]#[CH:24].[OH-].[Na+]>C(#N)C.C(Cl)Cl>[CH3:2][N:17]1[C:23]([CH3:24])=[CH:22][N:25]=[C:16]1[C:15]1[CH:18]=[CH:19][C:12]([C:11]([F:20])([F:21])[F:10])=[CH:13][CH:14]=1Participants
Conditions
- Temperature
- 65 °C
Procedure
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.
Workup
- temperaturecooled to 5° C
- temperaturecooled to 5° C.
- customThe organic layer was separated
- customthe solvent evaporated under reduced pressure, and 50 ml of toluene
- additionadded
- temperatureThe mixture was refluxed for 3 hours
- temperaturecooled
- customthe solvent evaporated under reduced pressure
- customthe residue recrystallized from isopropyl ether
Sources & evidence
- ORD record
- ord-8a361d1bf92d440e8c76e29a51b3f5f0
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05428037
Linked notes
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