1-Bromo-3-chloropropane → HCID 20505181, compound

Participants

Reaction Conditions

Reaction Steps

A 10 N aqueous solution of sodium hydroxide (39 cc) is added dropwise, in the course of 15 minutes and at a temperature of about 10° C., to a solution of 2-(pyrazinylmethyl)-isothiourea monohydrochloride (77.6 g) in distilled water (250 cc). After heating for 30 minutes at 70° C. and then cooling to 15° C., a 10 N aqueous solution of sodium hydroxide (47 cc) and then 1-bromo-3-chloropropane (66.5 g) are added 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 (280 cc in total). The organic extracts are combined, washed twice with distilled water (200 cc in total), dried over anhydous sodium sulphate and filtered. The solution obtained is poured onto neutral silica gel (80 g) contained in a column of diameter 2.7 cm; the column is then eluted with methylene chloride (900 cc). The first fraction (300 cc) is discarded; the second fraction (600 cc) is collected and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C. Pyrazinylmethyl 3-chloropropyl sulphide (59 g) is thus obtained in the form of a yellow-orange oil.

Provenance & Evidence