1-Bromo-3-chloropropane → HCID 20505184, compound

Participants

Reaction Conditions

Reaction Steps

A 10 N aqueous solution of sodium hydroxide (97 cc) is added dropwise, in the course of 15 minutes and whilst keeping the temperature below 14° C., to a solution of 2-(pyrid-4-yl-methyl)-isothiourea dihydrochloride (116.5 g) in distilled water (240 cc). After heating for 20 minutes at 83° C. and then cooling to 12° C., a 10 N aqueous solution of sodium hydroxide (60 cc) and then 1-bromo-3-chloropropane (81.5 g) are added, whilst stirring, and stirring is continued for 15 hours at a temperature of about 20° C. The reaction mixture is then extracted three times with methylene chloride (430 cc in total); the organic extracts are combined, washed with distilled water (250 cc) and dried over anhydrous sodium sulphate. After filtration, the solution obtained is poured onto neutral silica gel (125 g) contained in a column of diameter 3.2 cm; the column is then eluted with methylene chloride (1600 cc). The first fraction (400 cc) is discarded; the second fraction (1200 cc) is collected and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. Pyrid-4-yl-methyl 3-chloropropyl sulphide (81 g) is thus obtained in the form of a brown oil.

Provenance & Evidence