Iodine → 5-Iodo-2'-methyl salicylanilide

HRID 1105955Notes

Reaction equation

HRID 1105955 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5](=[O:13])[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8].[I:18]I>C(O)(=O)C>[I:18][C:11]1[CH:12]=[C:6]([C:5]([NH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=2[CH3:1])=[O:13])[C:7]([OH:8])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 807IodineHCID 7683182-hydroxy-N-(2-methylphenyl)benzamide

Product 1

HCID 205554145-Iodo-2'-methyl salicylanilide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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.

Workup

  1. temperaturemoderately cooling
  2. customreaction

Sources & evidence

ORD record
ord-f39cb54d53974989ac7f8e8de4b81709
Source dataset
uspto-grants-1982_01
Patent number
US04310682

Reaction notes

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