Bromine → HCID 12816529, compound

HRID 1105954Notes

Reaction equation

HRID 1105954 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([Cl:18])[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].[Br:19]Br>C(=S)=S>[Br:19][C:11]1[CH:12]=[C:6]([C:5]([NH:4][C:3]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:2]=2[CH3:1])=[O:13])[C:7]([OH:8])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 23274878N-(4-Chloro-2-methylphenyl)-2-hydroxybenzamide2×

Product 1

HCID 12816529HCID 12816529, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

135 g. of 2'-methyl-4'-chlorosalicylanilide is dissolved in 2,500 cc. of carbon disulfide with heating. Said solution is then rapidly cooled to form a finely dispersed suspension of 2'-methyl-4'-chlorosalicylanilide. A solution of 80 cc. of bromine in 250 cc. of carbon disulfide is added, drop by drop, at room temperature to said suspension with agitation. Said reaction mixture is allowed to stand over night. Thereby 210 g. of 5-bromo-2'-methyl-4'-chloro salicylanilide are obtained. Resulting compound (compound No. 1) forms colorless prism-shaped crystals having properties shown in Table 1 by recrystallizing from ethyl acetate.

Workup

  1. temperatureis then rapidly cooled
  2. customto form
  3. customat room temperature
  4. customreaction mixture
  5. waitto stand over night

Sources & evidence

ORD record
ord-d9acd43fc0cd4249a65b167c998578dd
Source dataset
uspto-grants-1982_01
Patent number
US04310682

Reaction notes

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