Pyridine → N-(2,3,4,5-tetrachlorobenzoyl)-3,4-dibromohexahydrophthalimide

HRID 1606399Notes

Reaction equation

HRID 1606399 reaction equation
[Br:1][CH:2]1[CH:12]([Br:13])[CH2:11][CH2:10][CH:4]2[C:5]([NH:7][C:8](=[O:9])[CH:3]12)=[O:6].N1C=CC=CC=1.[Cl:20][C:21]1[C:29]([Cl:30])=[C:28]([Cl:31])[C:27]([Cl:32])=[CH:26][C:22]=1[C:23](Cl)=[O:24]>C1C=CC=CC=1>[Cl:20][C:21]1[C:29]([Cl:30])=[C:28]([Cl:31])[C:27]([Cl:32])=[CH:26][C:22]=1[C:23]([N:7]1[C:8](=[O:9])[CH:3]2[CH:2]([Br:1])[CH:12]([Br:13])[CH2:11][CH2:10][CH:4]2[C:5]1=[O:6])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 54637972,3,4,5-Tetrachlorobenzoyl chlorideHCID 215427963,4-Dibromohexahydrophthalimide

Product 1

HCID 21542798N-(2,3,4,5-tetrachlorobenzoyl)-3,4-dibromohexahydrophthalimide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,4-Dibromohexahydrophthalimide (0.10 mole), benzene (300 ml) and pyridine (0.11 mole) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2,3,4,5-Tetrachlorobenzoyl chloride (0.10 mole) is then added dropwise to the flask with stirring at room temperature. After the addition is completed the reaction mixture is heated at reflux with continued stirring for a period of about 1 hour. After this time the reaction mixture is filtered and the filtrate is washed with water. The washed filtrate is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-(2,3,4,5-tetrachlorobenzoyl)-3,4-dibromohexahydrophthalimide.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionAfter the addition
  4. temperatureis heated
  5. temperatureat reflux
  6. stirringwith continued stirring for a period of about 1 hour
  7. filtrationAfter this time the reaction mixture is filtered
  8. washthe filtrate is washed with water
  9. dry with materialThe washed filtrate is then dried over anhydrous magnesium sulfate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-1e165ab5283d46c68ff97a4e46c7baa8
Source dataset
uspto-grants-1976_04
Patent number
US03953397

Reaction notes

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