Benzoyl chloride → N-(6-Ethoxypyridin-3-yl)thiourea

Participants

Reaction Steps

A solution of 12 g of 3-amino-6-ethoxypyridine in 30 ml of acetone was admixed with a solution of 7.6 g of potassium thiocyanate in 60 ml of acetone, and under stirring, 15.4 g of benzoyl chloride was added dropwise. The mixture was then boiled for 10 minutes. The reaction mixture was poured into ice-water and the resulting crystals (m.p. 130°-133° C.) were recovered by filtration and boiled with 50 ml of 10% sodium hydroxide for 15 minutes. After cooling, crystals (m.p. 142°-146° C.) of 6-ethoxy-3-pyridylthiourea were obtained. These crystals were dissolved in 150 ml of hot 10% potassium hydroxide, and after addition of 37 g of lead acetate, the mixture was stirred at 80° C. for 20 minutes. The precipitated lead sulfide was filtered off and the filtrate was neutralized to give 5 g of 6-ethoxy-3-pyridylcyanamide as colorless needles melting 102°-104° C.

Provenance & Evidence