D-Glucosamine → 1-(1,2,3,4-Tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-isothiocyano-1,2,3,4-tetrahydronaphthalene (1.89 g, 10 mmol), prepared as in Example 10, and D-(+)-glucosamine (1.78 g, 10 mmol) was stirred at 90° C. until homogenous and then 0.8 mL of acetic acid was added. The mixture was stirred at 90° C. for 30 minutes and then cooled. The solvents were removed by rotary evaporation and the residue was co-evaporated with toluene (2×25 mL). The residue was dissolved in acetic acid and heated at 90° to 100° C. for 30 minutes. The mixture was cooled and triturated with acetone giving a crystalline material. The material was isolated by filtration and the filter residue washed with acetone. Drying gave 4-(1R,2R,3S,4)-tetrahydroxybut-1-yl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (1.48 g, 4.23 mmol).

Provenance & Evidence