Thionyl Chloride → 1h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-,hydrochloride
Reaktionsgleichung
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([CH2:18][Cl:19])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH3:20]>>[ClH:3].[Cl:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([CH2:18][Cl:19])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH3:20]Komponenten
Versuchsvorschrift
Thionyl chloride (5 ml) is added to 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole (3.56 g), and the solution is stirred for 20 minutes at room temperature and then for 20 minutes at 80° C. After excess thionyl chloride is removed through evaporation under reduced pressure, the residue is dissolved in chloroform (10 ml), and crystallization is performed by adding hexane. The crystals are separated through filtration, washed in hexane, and dried. Thus, 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole hydrochloride (4.07 g) is obtained. 1H-NMR (CDCl3, δ): 3.01 (3H, s), 4.68 (2H, s), 5.61 (2H. s), 6.71 (1H, d, J=7.5 Hz), 7.24-7.29 (1H, m), 7.38 (1H, t, J=7.7 Hz), 7.44 (1H, s), 7.52 (2H, d, J=8.2 Hz), 7.92 (1H, d J=8.4 Hz).
Aufarbeitung
- waitfor 20 minutes at 80° C
- customAfter excess thionyl chloride is removed through evaporation under reduced pressure
- dissolutionthe residue is dissolved in chloroform (10 ml)
- customcrystallization
- additionby adding hexane
- customThe crystals are separated through filtration
- washwashed in hexane
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-62c727f2abeb4eb3a39ee878752d630f
- Quelldatensatz
- uspto-grants-2002_04
- Patentnummer
- US06369092B1
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