Reaktion #47117

Reaktionsgleichung

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

Ausbeute 59.2%

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

Ausbeute 59.2%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water, brine
2. 2
   Trocknenthe organic layer is dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue is purified by chromatography on silica gel
6. 6
   Waschengradient elution with heptane:EtOAc (70:30-60:40)

Vorschrift

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).

Quelle