Carbon Dioxide → HCID 10953610, compound

Participants

Reaction Steps

A mixture of pyrrole (6.7 g., 0.10 mole) and thiourea (7.6 g., 0.10 mole) in 50% aqueous ethanol (500 ml.) was stirred at room temperature under nitrogen while a solution of potassium iodide (16.6 g., 0.10 mole) and iodine (12.7 g., 0.05 mole) in water (100 ml.) was added dropwise. The solution was cooled to 0° and a solution of propyl iodide (18 g., 0.105 mole) in methanol (20 ml.) was added followed by the dropwise addition of a solution of potassium hydroxide (5.6 g.) in 50% aqueous methanol (40 ml.). The mixture was stirred for a further 1.5 hours at room temperature and the solution then neutralized by the addition of solid carbon dioxide. The reaction mixture was poured into a solution of sodium chloride (25 g.) in water (100 ml.) and the solution extracted with methylene chloride (3×50 ml.). The organic extracts were combined, dried over sodium sulphate and the solvent evaporated to give an oil which was distilled under reduced pressure to yield 2-n-propylthiopyrrole (1.0 g.), B.P. 115° at 15 mm.

Provenance & Evidence