Pyridine → HCID 54422056, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of cyclohexane (60 ml.), pyridine (1.43 ml.) and 2-hexadecanoyloxy-1-(hexadecanoyloxymethyl)ethyl hydrogen glutarate (B) (11.0 g.) was warmed to 35° C. The solution obtained was added dropwise during 45 minutes to a stirred solution of thionyl chloride (1.23 ml.) in cyclohexane (25 ml.) at 35° C. The mixture was then stirred for a further 1.5 hours at 35° C., cooled to 15° C. and a solution of triclosan (4.68 g.) and pyridine (1.56 ml.) in cyclohexane (20 ml.) added during 15 minutes. The mixture was stirred at ambient temperature for 16 hours, warmed to 35° C. and washed first with 0.5 M hydrochloric acid (100 ml.) and then with water (3×100 ml.), also heated to 35° C. The mixture was then dried (MgSO4) and evaporated to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-hexadecanoyloxy-1-(hexadecanoyloxymethyl)ethyl glutarate as a white solid, m.p. 44°-46° C., identical with the material obtained in Example 4 as judged by its NMR and mass spectral properties.

Provenance & Evidence