3,4,5,6-Tetrachlorophthalimide → N-(2,4,6-tribromobenzoyl)-3,4,5,6-tetrachlorophthalimide

HRID 1605207Notes

Reaction equation

HRID 1605207 reaction equation
[K].[Cl:2][C:3]1[C:13]([Cl:14])=[C:12]([Cl:15])[C:11]([Cl:16])=[C:5]2[C:6]([NH:8][C:9](=[O:10])[C:4]=12)=[O:7].[Br:17][C:18]1[CH:26]=[C:25]([Br:27])[CH:24]=[C:23]([Br:28])[C:19]=1[C:20](Cl)=[O:21]>O1CCOCC1>[Br:17][C:18]1[CH:26]=[C:25]([Br:27])[CH:24]=[C:23]([Br:28])[C:19]=1[C:20]([N:8]1[C:9](=[O:10])[C:4]2=[C:3]([Cl:2])[C:13]([Cl:14])=[C:12]([Cl:15])[C:11]([Cl:16])=[C:5]2[C:6]1=[O:7])=[O:21]

Participants

5

Reactant 3

HCID 740773,4,5,6-TetrachlorophthalimideHCID 5462222PotassiumHCID 112342662,4,6-tribromobenzoyl Chloride

Product 1

HCID 21546569N-(2,4,6-tribromobenzoyl)-3,4,5,6-tetrachlorophthalimide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The potassium salt of 3,4,5,6-tetrachlorophthalimide (0.10 mole) and dioxane (1200 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2,4,6-Tribromobenzoyl chloride (0.10 mole) is then added dropwise, with stirring, to the reaction mixture at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 1 hour. After this time the reaction mixture is filtered and the filtrate is stripped of solvent to yield the desired product N-(2,4,6-tribromobenzoyl)-3,4,5,6-tetrachlorophthalimide.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionAfter the addition
  4. temperatureis heated
  5. temperatureat reflux for a period of about 1 hour
  6. filtrationAfter this time the reaction mixture is filtered

Sources & evidence

ORD record
ord-a05d228dd4fe49e0968ad0bd14e0035e
Source dataset
uspto-grants-1976_04
Patent number
US03950307

Reaction notes

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