Triethylamine → HCID 160113003, compound

Participants

Reaction Steps

To a solution of 3,7-diiodo-phenoselenazin-ylium iodide hydrate (2.34 g) (prepared as above for Compound 2) in methanol (300 cm3) was added triethylamine (1.0 cm3) followed by dihexylamine (5 cm3). The reaction was stirred for 24 hours. The residue remaining after removal of the methanol was taken up in dichloromethane and washed with dilute hydriodic acid (5% w/w) followed by water. The organic phase was isolated and dried (MgSO4). Flash column chromatography over silica gel 60 Å was performed on the crude material using a mobile phase of 85/15 methanol/water containing 3% w/v ammonium acetate. After isolation of the desired fractions and removal of the methanol, the product was extracted from the aqueous phase using dichloromethane. Concentration of the dichloromethane in vacuo and addition of an excess of diethyl ether resulted in precipitation of the product. The product was collected by filtration, washed with diethyl ether and dried to give 3,7-bis-(N,N-dihexylamino)-phenoselenazin-5-ylium iodide as a dark coloured powder, in 21% yield.

Provenance & Evidence