Sulfuric Acid → HCID 21272626, compound

Participants

Reaction Steps

1.9 Grams of lithium aluminum hydride was added to about 50 ml of dry tetrahydrofuran. Then 1.3 ml of sulfuric acid was added by means of a syringe with cooling. The resulting slurry was stirred at room temperature for 1 hour and then a tetrahydrofuran solution of 3.0 g of 2-cyano-1-(2-thienylmethyl)-1H-imidazole was added and the mixture was stirred for 16 hours. The reaction mixture was quenched with 1.9 ml of water, 1.9 ml of 15% aqueous sodium hydroxide solution, and 5.7 ml of water. The mixture was then filtered and the solid was washed with ethyl acetate. The filtrate was then partitioned between water and ethyl acetate. The ethyl acetate layer was separated, dried over sodium sulfate and concentrated to give a yellow oil. A solution of 0.7 g of this oil in 300 ml of ether was prepared and a solution of 3.6 g of 4-toluenesulfonic acid in ethanol was added. The solid which formed was separated by filtration and dried to give 2-aminomethyl-1-(2-thienylmethyl)-1H-imidazole 4-toluenesulfonate melting at about 129°-131° C.

Provenance & Evidence