1-Bromo-3-chloropropane → Quinol-3-ylmethyl 3-chloropropyl sulphide

Participants

Reaction Conditions

Reaction Steps

A 10 N aqueous solution of sodium hydroxide (40.8 cc) is added in the course of 9 minutes, and whilst allowing the temperature to rise to 10° C., to a solution, cooled to 1° C., of 2-(quinol-3-ylmethyl)-isothiourea dihydrochloride (59.2 g) in distilled water (100 cc). After heating for 20 minutes at a temperature of about 70° C. and then cooling to 12° C., a 10 N aqueous solution of sodium hydroxide (25 cc) is added dropwise in the course of 5 minutes. 1-Bromo-3-chloropropane (33.6 g) is then added and stirring is continued for 20 hours at a temperature of about 20° C. The reaction mixture is then extracted three times with methylene chloride (400 cc in total). The organic extracts are combined, washed with distilled water (100 cc), dried over anhydrous sodium sulphate and concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C. so as to bring the volume to about 100 cc. The solution thus obtained is chromatographed on neutral silica gel (250 g) contained in a column of diameter 3.8 cm. Elution is carried out with methylene chloride (1500 cc), one 600 cc fraction and one 900 cc fraction being collected. The latter fraction is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C. Quinol-3-ylmethyl 3-chloropropyl sulphide (9.2 g) is thus obtained in the form of a yellow oil.

Provenance & Evidence