Sodium Acetate → 5-Iodo-2'-methyl salicylanilide

Reaction equation

[I:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12]([O-])(=O)[CH3:13].[Na+]>[Cu].CC1C=CC=CC=1>[I:1][C:2]1[CH:10]=[C:6]([C:7]([NH:9][C:6]2[CH:10]=[CH:2][CH:3]=[CH:4][C:12]=2[CH3:13])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

Procedure

37.1 g. of 5-iodo salicylamide, 43.6 g. of 2-methyl benzene, 10 g. of anhydrous sodium acetate, 1 g. of copper bronze are mixed together and heated under reflux for 4 hours. The molten mass obtained is dissolved in alcohol. Said solution is filtered and concentrated by evaporation. 5-iodo-2'-methyl salicylanilide is obtained thereby. Said compound is then dissolved in about 5 times its amount by weight of a mixture of glacial acetic acid and ethyl acetate (1:1). A solution of 40.8 g. of bromine in 30 cc. of glacial acetic acid is added to said solution to obtain 5-iodo-2'-methyl-4'-bromo salicylanilide. Resulting compound (compound No. 5) forms colorless needle-shaped crystals having properties shown in Table 5 by recrystallizing from ethanol.