Iodine chloride → 1-(4-Amino-3-iodo-5-methyl-phenyl)-1,2,4-triazole

Participants

Reaction Steps

Iodine monochloride (5.103 g) was added dropwise to a stirred solution of 1-(4-amino-3-methylphenyl)-1,2,4-triazole (5.22 g) and sodium acetate (2.583 g) in acetic acid (100 cm3). After 16 hours volatile material was removed in vacuo and the residue was partitioned between dichloromethane (100 cm3) and sodium carbonate solution (50 cm3). The organic phase was washed with sodium thiosulphate solution (10 g in 50 cm3 water), dried (MgSO4) and evaporated to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate. Combination and evaporaton of the appropriate fractions gave a solid which was recrystallised from ethyl acetate-ether to afford the title compound, m.p. 151°-154° (3.1 g).

Provenance & Evidence