Dimethylformamide → 3-Chloro-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113747Notes

Reaction equation

HRID 2113747 reaction equation
O[C:2]1[C:3](=[O:14])[NH:4][C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C=O)C.C(Cl)(=O)C([Cl:23])=O>ClCCl>[Cl:23][C:2]1[C:3](=[O:14])[NH:4][C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 547071273-Hydroxy-4-phenyl-1H-pyrrole-2,5-dione

Product 1

HCID 540140893-Chloro-4-phenyl-1H-pyrrole-2,5-dioneYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-hydroxy-4-phenyl-1H-pyrrole-2,5-dione (25.0 g, 0.13 mol) in dichloromethane (600 mL) under nitrogen was added DMF (36 mL). The suspension was cooled to ice temperature and treated with oxalyl chloride (40.0 g, 0.32 mol). The reaction mixture was subsequently refluxed overnight. After cooling to room temperature silica gel was added and the reaction mixture evaporated to dryness and subjected to flash chromatography (hexane:EtOAc 80:20). Trituration with dichloromethane, filtration and drying gave 17.6 g (64%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.96-7.89 (m, 2H), 7.88-7.77 (bs, 1H), 7.55-7.45 (m, 3H).

Workup

  1. temperatureThe suspension was cooled to ice temperature
  2. additionwas added
  3. customthe reaction mixture evaporated to dryness
  4. filtrationTrituration with dichloromethane, filtration
  5. customdrying

Sources & evidence

ORD record
ord-27646eadc0b241dcadca923e8919436b
Source dataset
uspto-grants-2008_10
Patent number
US07432288B2

Reaction notes

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