Dimethylformamide → HCID 20368819, compound

Participants

Reaction Steps

To 2-phenyl-4,5-dihydro-naphtho[1,2-d]imidazole (2.46 g.) dissolved in 10 ml. of dimethylforamide, 0.5 g. of 55% NaH (mineral oil dispersion) and 1.41 g. of methyl iodide are added. After stirring for two hours at room temperature, and for one hour at 60° C., the mixture is poured into ice water. The resulting solid precipitate is dissolved in benzene and chromatographed through a silica gel column and eluted with benzene containing 10% of ethyl ether for separating the two methylated isomers. The first eluted isomer (1.66 g.) melts at 150° C. (from ethanol) while the second (0.79 g.) melts at 141°-3° C. By operating according to the procedure described in Example 1, utilizing as the starting material 2-bromo-1-indanone, 2-phenyl-1,8-dihydro-indeno[1,2-d]imidazole (m.p. 231-2) is obtained which is in turn methylated according to the procedure described above to give 1-methyl-2-phenyl-8H-indeno[1,2-d]-imidazole, 3-methyl-2-phenyl-8-indeno[1,2-d]imidazole.

Provenance & Evidence