2-Mercaptobenzoic Acid → HCID 19426235, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-diiodonaphthalene (38.0 grams, 0.10 mole), thiosalicyclic acid (30.8 grams, 0.20 mole), potassium carbonate (27.3 grams, 0.20 mole) and N,N-dimethylformamide (200 ml) was heated and stirred at 130°-135° C. for 8 hours. An isolated sample showed mostly starting material and half-reacted product. More N,N-dimethylformamide (50.0 ml) was added and the reaction mixture was heated for an additional 30 hours at about 150° C. The reaction mixture was drowned into water (500 ml) and the "milky" mixture was filtered using Celite filter aid to remove the unreacted 2,6-diiodonaphthalene. The filtrate was acidified with concentrated HCl to precipitate the product which was collected by filtration and washed with water. The wet cake was ground using a mortar and pestle and then reslurried in methanol. After collecting the solid by filtration, washing with methanol and drying in air, forty grams of crude product were obtained.

Provenance & Evidence