3-Chloropropionyl chloride → HCID 21465211, Verbindung

Reaktionsgleichung

[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][C:8](Cl)=[O:9].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:19][C:18](=[O:20])[NH:17][C:16]=2[CH:21]=1>CN(C=O)C>[Cl:5][CH2:6][CH2:7][C:8]([C:13]1[C:12]([Cl:11])=[CH:21][C:16]2[NH:17][C:18](=[O:20])[NH:19][C:15]=2[CH:14]=1)=[O:9]

Komponenten

Versuchsvorschrift

44.68 g of aluminium chloride (0.335 mol) are initially introduced into a reaction flask. 4.9 ml of DMF are slowly added dropwise with stirring, the temperature rising to approximately 56° C. 6.9 ml of 3-chloropropionyl chloride (0.072 mol) are added to this mixture. 8.07 g of 6-chloro-2,3-dihydrobenzimidazol-2-one (0.048 mol) are then slowly added in portions and the mixture is stirred at 80° C. for one hour. After completion of the reaction the reaction mixture obtained is stirred into 400 g of ice, and the precipitate is filtered off with suction and washed with plenty of water and small amounts of acetone. The reaction leads to a slightly more non-polar product which can be separated by thin-layer chromatography using an eluent consisting of-chloroform and methanol in the mixture ratio 9:1. Yield: 9.72 g of 5-(3-chloro-1-oxopropyl)-6-chloro-2,3-dihydrobenzimidazol-2-one (78.2% of theory); m.p.: 201°-204° C.