Phosphoric Acid → HCID 129690005, compound

Participants

Reaction Steps

173 g (1.69 moles) of bis-dimethylaminomethane were added, while cooling, to a solution of 173 g of phosphoric acid in 1,600 ml of glacial acetic acid, 185.6 g (1.0 mole) of ferrocene were then added and the mixture was warmed for 5 hours under a nitrogen atmosphere on a waterbath. The reaction mixture was then cooled to room temperature and diluted with 2,200 ml of water and unconverted ferrocene was removed by extraction with ether. The remaining reaction mixture was rendered alkaline by adding 480 g of sodium hydroxide, diluted with a further 800 ml of water and then extracted three times with ether. The organic phase was separated off, washed with water and, after drying over sodium sulfate, concentrated. 204 g (89% of theory) of N,N-dimethylamino-methylferrocene remained and were taken up in 215 ml of methanol. 215 ml (500 g) of methyl iodide were added to the resulting solution and the mixture was heated for 5 minutes on a boiling waterbath and, after cooling to room temperature, poured into 3,200 ml of ether. The product, which was initially obtained as an oil, crystallised on trituration. In this way, 323 g (83.9% of theory) of N,N-dimethylamino-methylferrocene methoiodide with a melting point of 213° C (decomposition) were obtained.

Provenance & Evidence