p-Chlorothiophenol → HCID 43135474, compound

Participants

Reaction Steps

In similar fashion to the synthesis of (XV), 4-chlorothiophenol (28.9 grams, 0.2 mol) was treated with sodium hydroxide (40 mL of 20% aqueous solution) and then combined with 1,3-dibromopropane (160 grams, 0.8 mol) and refluxed for 4 hours. The mixture was cooled, the aqueous layer separated and neutralized with 20% sodium hydroxide solution, and the lower layer washed five times with water and distilled at 1 mm Hg. The main fraction was collected between 120°-130° C. as a colorless oil (47.5 grams, 90%) which crystallized on standing to give 4-chlorothiophenoxy propyl bromide (XIX) is then further reacted with acetohydroxamic acid as described previously in Example 1 and hydrolyzed to give the 3-(4-chlorothiophenoxy)propyloxamine hydrochloride (XX). This in turn is reacted with isopropyl dicyanodiamide as described previously in Example 1 to give the title compound (XXI).

Provenance & Evidence