Hydrochloric Acid → HCID 178527873, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of aminoacetaldehyde dimethylacetal (5.45 ml., 0.05 mole) and 2-thiophenecarboxaldehyde (4.67 ml., 0.05 mole) was heated at 100° C. for 2 hours and the reaction mixture was cooled in ice and diluted with ethyl alcohol (50 ml.). Sodium borohydride (1 g) was added to the solution and the reaction mixture was stirred for 17 hours. The solvent was removed under vacuum, ethyl acetate (50ml) was added, and the solution was washed with water and brine and dried over sodium sulfate. The mixture was filtered and the solvent was removed under vacuum. The resultant oil was diluted with ethyl alcohol (69 ml), potassium thiocyanate (5.59 g, 0.0575 mole) in water (115 ml) followed by concentrated hydrochloric acid (11.5 ml) and the solution was heated at reflux for 2.5 hours. The solvent was removed until an oil came out of solution at which point the reaction mixture was cooled with ice, diluted with water, and the crude product was filtered. The product was first recrystallized from a mixture of ethyl acetate-hexane followed by ethyl acetate to give 1-(2-thienylmethyl)imidazole-2-thiol, melting at 130°-131° C. (2.79 g., 28%).

Provenance & Evidence