Pyridine → HCID 12397650, compound

HRID 1355339Notes

Reaction equation

HRID 1355339 reaction equation
S(Br)([Br:3])=O.N1C=CC=CC=1.[C:11]1([C:17]2[C:18]([O:20][C:21](=[O:23])[CH:22]=2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br:3][C:22]1[C:21](=[O:23])[O:20][C:18](=[O:19])[C:17]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 99174Phenylmaleic anhydride

Product 1

HCID 12397650HCID 12397650, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

At 10° C., first 40.2 g (193 mmol) of thionyl bromide and then 15.3 g (193 mmol) of pyridine were added dropwise with stirring to 16.8 g (97 mmol) of phenylmaleic anhydride in 200 ml of toluene. The mixture was stirred at 10° C. for 30 min, heated at 75° C. for 30 min using a preheated heating bath and allowed to cool, and excess thionyl bromide was removed at 65° C. under reduced pressure. The mixture was then stirred with 150 ml of toluene and filtered, and the residue was washed twice with in each case 200 ml of toluene, and the filtrate was concentrated under reduced pressure. The crude product (9.3 g) still contained 25% of unreacted starting material and was used without further purification.

Workup

  1. temperatureheated at 75° C. for 30 min
  2. temperatureto cool
  3. customexcess thionyl bromide was removed at 65° C. under reduced pressure
  4. stirringThe mixture was then stirred with 150 ml of toluene
  5. filtrationfiltered
  6. washthe residue was washed twice with in each case 200 ml of toluene
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customwas used without further purification

Sources & evidence

ORD record
ord-5c9dddc3322342b3b698aa100bcb8ae7
Source dataset
uspto-grants-2003_07
Patent number
US06586369B1

Reaction notes

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