Tetrahydrofuran → HCID 19862555, compound

Participants

Reaction Steps

15 ml of acetic anhydride and 7.5 ml of formic acid (98-100%) are mixed carefully at 0° and subsequently heated to 50° on a water-bath for 1 hour. The mixed anhydride formed is diluted with 25 ml of abs. tetrahydrofuran and 4.52 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)imidazole are introduced in small portions into the solution obtained. The reaction mixture is left to stand at room temperature for 1 hour and evaporated under reduced pressure on a rotary evaporator. The residue is treated with a small amount of ice-cold water and saturated sodium bicarbonate is added up to a weakly alkaline reaction. After three-fold extraction with methylene chloride, the combined organic extracts are washed once with water and once with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue is recrystallized from ethyl acetate/n-hexane and there is obtained 1-[N-formyl-N-(4-hydroxy-3,5-di-tert.-butylbenzyl)amino]imidazole of m.p. 167°.

Provenance & Evidence