Sodium Carbonate → 2-[[(4-ethoxy-3-methyl-2-pyridyl)methyl]thio]5,7-dihydro-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one

Participants

Reaction Steps

A mixture of 10.5 g of sodium ethylate. 20 g of sodium carbonate and 400 ml of ethanol was stirred at 50° under argon for 30 minutes and then treated with 7 g of 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-4-nitro-2-pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(lH)-one. After stirring at 50° for 5 hours under argon the reaction mixture was concentrated in vacuo. The residue was treated with methylene chloride and buffered by means of glacial acetic acid; the methylene chloride solution was extracted with sodium bicarbonate solution, dried and concentrated. The residue was chromatographed on silica gel while eluting with methylene chloride/ethyl acetate (3:1), the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. There was obtained 2-[[(4-ethoxy-3-methyl-2-pyridyl)methyl]thio]5,7-dihydro-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(lH)-one which melts at 175-176° after recrystallization from ether.

Provenance & Evidence