Pyridine → HCID 12397650, compound

HRID 1840250Notes

Reaction equation

HRID 1840250 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 munol) 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-5bc32b9b6493493e8c0e9097295b5344
Source dataset
uspto-grants-2004_01
Patent number
US06680283B1

Reaction notes

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