Diethyl Ether → 2-[[2-Methyl-4-((1-methylethoxy)carbonylamino)-phenyl]amino]-1-pyrroline, hydrochloride

Participants

Reaction Steps

To 1.2 g (4.6 mmole) of the product compound of Example 9 in 30 ml of acetonitrile was added a 10% excess of phosgene in toluene. The mixture was stirred at 20° in the absence of moisture for 16 hours, at which time a large excess (20 ml) of isopropyl alcohol was added. The reaction mixture was stirred at 20° until reaction was complete, as indicated by thin-layer chromatography on silica gel (9:1 ethanol/concentrated aqueous ammonia or 74:25:1 dichloromethane/ethanol/ammonia). The product was taken up in an eight-fold excess of diethyl ether and recovered as an oil by concentrating the extract. The title compound crystallized upon standing. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Provenance & Evidence