Pyridine → 3-Chloro-4-phenylfuran-2,5-dione

HRID 1355332Notes

Reaction equation

HRID 1355332 reaction equation
[C:1]1([C:7]2[C:8]([O:10][C:11](=[O:13])[CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:16][C:12]1[C:11](=[O:13])[O:10][C:8](=[O:9])[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl Chloride2×HCID 99174Phenylmaleic anhydride

Product 1

HCID 234471953-Chloro-4-phenylfuran-2,5-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
11 °C

Procedure

With ice-cooling, 10.0 g (57 mmol) of phenylmaleic anhydride were added to 57 ml of thionyl chloride, and the mixture was, over a period of 10 min, admixed dropwise with 9.08 g (115 mmol) of pyridine, the temperature being maintained at 10-12° C. The mixture was stirred at 10-12° C. for 30 min, heated at 75° C. for 10 min. using a preheated heating bath and allowed to cool, and excess thionylchloride was stripped off at 60° C. at reduced pressure. The residue was then boiled with 120 ml of toluene and filtered, and the residue was washed with 50 ml of hot toluene. The filtrate was concentrated under reduced pressure, titrated with petroleum ether and dried. Yield: 8.5 g, m.p. 82-83° C.

Workup

  1. temperatureWith ice-cooling
  2. temperatureheated at 75° C. for 10 min.
  3. temperatureto cool
  4. customwas stripped off at 60° C. at reduced pressure
  5. filtrationfiltered
  6. washthe residue was washed with 50 ml of hot toluene
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-37800c3def4042d9926457a3ba7f4d01
Source dataset
uspto-grants-2003_07
Patent number
US06586369B1

Reaction notes

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