Triethylamine → 5,6-Dihydropyrrolo[1,2-c]imidazol-7-one

Temperature

70 °C

3-Bromo-1-(1H-imidazol-4-yl)-1-propanone (28.5 g) was suspended in acetonitrile (1100 ml) and the suspension was warmed to 70° C. A solution of triethylamine (15.3 ml) in acetonitrile (25 ml) was slowly added dropwise and the mixture was stirred at 70° C. for 2 h. Triethylamine (25 ml) was further added and the mixture was stirred for 30 min. The reaction mixture was cooled to room temperature and the insoluble material was filtered off. The solvent was evaporated and the residue was dissolved in ethyl acetate again. The insoluble material was filtered off and the solvent was evaporated. The resulting residue was subjected to silica gel column chromatography (eluent; dichloromethane:methanol containing ammonia (5%)=10:1) for purification to give the title compound (6.67 g) as a colorless powder.

1. stirringthe mixture was stirred for 30 min
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationthe insoluble material was filtered off
4. customThe solvent was evaporated
5. dissolutionthe residue was dissolved in ethyl acetate again
6. filtrationThe insoluble material was filtered off
7. customthe solvent was evaporated
8. additionThe resulting residue was subjected to silica gel column chromatography (eluent; dichloromethane:methanol containing ammonia (5%)=10:1) for purification

ORD record

ord-f8a3c960442f4a498a8fdde575af4764

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141598B2