Réaction #47117

Équation de réaction

2-(methylthio)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydroiodide

cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-1H-imidazole hydroiodide

triethylamine

phenyl chloroformate

→

product 548

Rendement 59.2%

2-(Methylthio)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid phenyl ester

Rendement 59.2%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water, brine
2. 2
   Séchagethe organic layer is dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Autreevaporated
5. 5
   AutreThe residue is purified by chromatography on silica gel
6. 6
   Lavagegradient elution with heptane:EtOAc (70:30-60:40)

Mode opératoire

To a solution of 2-(methylthio)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydroiodide (42) (1.00 mg, 2.52 mmol), triethylamine (0.528 mL, 0.379 mmol), 4-dimethylamino-pyridine (10 mg) in dichloromethane (20 mL) is added phenyl chloroformate (0.379 mL, 3.02 mmol), and the mixture is stirred at rt overnight. The reaction mixture is diluted with dichloromethane and washed with water, brine, and the organic layer is dried (MgSO4), filtered, and evaporated. The residue is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 0.58 g of the product 548. 1H NMR (CDCl3) δ 7.25-6.95 (m, 11H), 6.95-6.80 (m, 2H), 6.80-6.70 (m, 2H), 5.80-5.65 (m, 2H), 2.62 (s, 3H). MS: m/z 389 (M++1).

Source