Hydrochloric Acid → Ethyl 3-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)imidazol-2-yl-thio]propionate

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Reaction Conditions

Reaction Steps

A mixture of 1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydro-imidazole-2-thione (1 g, 4.3 mmol), prepared as in Example 9, ethyl acrylate (4.7 mL, 43 mmol) and hydrochloric acid (1N in ether, 8.7 mL, 8.7 mmol) in 20 mL of ethanol was heated at 80° C. under nitrogen for approximately 5 hours. The mixture was allowed to cool, concentrated and partitioned between saturated sodium bicarbonate solution and methylene chloride. The organic layer was separated and dried (K2CO3), filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (99: 1) to give ethyl 3-[1-(1,2,3,4-tetrahydronaphthalen-2-yl) imidazol-2-yl-thio]propionate (1.36 g, 4.1 mmol).

Provenance & Evidence