Carbon Disulfide → HCID 20228703, compound

Participants

Reaction Steps

To a solution of potassium hydroxide (0.67 g) and carbondisulfide (0.91 g) in a mixture of water (1.5 ml) and ethanol (50 ml) was added 7-methyl-2-(3-amino-4-hydroxyphenyl)imidazo[1,2-a]pyridine (2.4 g) and the mixture was refluxed for 5 hours under stirring. To the reaction mixture was added a solution of 2-chloromethylpyridine hydrochloride (4.9 g) and potassium carbonate (3.8 g) in a mixture of water (5 ml) and ethanol (20 ml) at ambient temperature and the resultant mixture was stirred for 3 hours. The precipitate collected by filtration, was suspended in a mixture of water, tetrahydrofuran and ethyl acetate and the mixture was adjusted to pH 11 with 20% potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to afford a crystalline residue, which was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 5-(7-methylimidazo[1,2-a]pyridin-2-yl)-2-(pyridin-2-ylmethylthio)benzoxazole (1.6 g). mp. 184°-185° C. (dec.).

Provenance & Evidence