2-(Chloromethyl)-3-methylpyridine → 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-2-pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one

Participants

Reaction Steps

A suspension of 5.2 g of 5.7-dihydro-2-mercapto-5,5,7,7 -tetramethylindeno[5,6-d]imidazol-6(1H )-one and 2.6 g of potassium t-butanolate is treated under argon with a solution of 3 g of 2-chloromethyl-3-methylpyridine in 30 ml of t-butanol and the mixture is stirred for 18 hours. After concentrating the mixture the residue is acidified with glacial acetic acid and dissolved in methylene chloride, whereupon 10% sodium bicarbonate solution is added thereto. the mixture is extracted and the methylene chloride solutlon is dried and concentrated. The thus-obtained crude product is chromatographed on silica gel and purified with methylene chloride/ethyl acetate (1:1), the medium pressure flash chromatography method being used and the pressure being produced with nitroqen gas. The 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-2 -pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H )-one which is obtained from ethyl acetate-n-hexane melts at 161°-164°.

Provenance & Evidence