Iodine → 5-Iodo-2'-methyl salicylanilide

Participants

Reaction Steps

45.4 g. of 2'-methyl salicylanilide are dissolved in about 170.0 g. of glacial acetic acid. A solution 50.8 g. of iodine in 20 g. of glacial acetic acid is added, drop by drop, to said solution with agitation and moderately cooling. After said reaction is completed, 70.6 g. of 5-iodo-2'-methyl salicylanilide are obtained by filtration. Said compound is dissolved in 500 cc. of glacial acetic acid and 150 g. of ethyl acetate. 7.0 g. of chlorine are introduced into said solution under existence of a little amount of iron powder at about 40° C. to obtain 5-iodo-2'-methyl-4'-chloro salicylanilide. Resulting compound (compound No. 3) forms slightly yellowish powder having properties shown in Table 3 by recrystallizing from ethyl acetate.

Provenance & Evidence