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

HRID 2113739Notes

Reaction equation

HRID 2113739 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.N1C=CC=CC=1.S(Cl)([Cl:22])=O>>[Cl:22][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

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 99174Phenylmaleic anhydride

Product 1

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

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of phenylmaleic anhydride (5.74 mmol, 1.0 g) in thionyl chloride (6.0 mL) was added drop wise pyridine (11.4 mmol, 0.9 g). The reaction mixture was stirred for 60 min at 0° C., followed by heating to 75° C. for 20 min. The reaction mixture was cooled to room temperature and the thionyl chloride was removed in vacuo. The crude residue was suspended in toluene (10 mL), refluxed for 10 min., followed by filtration of the hot mixture. The filtrate was concentrated to give 1.15 g (96%) of the title. 1H NMR (400 MHz, CDCl3) δ 8.05-8.00 (m, 2H), 7.59-7.51 (m, 3H).

Workup

  1. temperatureby heating to 75° C. for 20 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe thionyl chloride was removed in vacuo
  4. temperaturerefluxed for 10 min.
  5. filtrationfollowed by filtration of the hot mixture
  6. concentrationThe filtrate was concentrated
  7. customto give 1.15 g (96%) of the title

Sources & evidence

ORD record
ord-b110f2c22e584039a15870726e91dd67
Source dataset
uspto-grants-2008_10
Patent number
US07432288B2

Reaction notes

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