Pyrrole → Phenyl(1H-pyrrol-2-YL)methanone

HRID 1090850Notes

Reaction equation

HRID 1090850 reaction equation
CN(C)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)(=O)C(Cl)=O.[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C([O-])(=O)C.[Na+]>ClCCCl>[C:3]([C:19]1[NH:18][CH:22]=[CH:21][CH:20]=1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8027PyrroleHCID 11916N,N-DimethylbenzamideHCID 65578Oxalyl chlorideHCID 517045Sodium Acetate

Product 1

HCID 24370Phenyl(1H-pyrrol-2-YL)methanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N,N-dimethylbenzamide (48.0 g, 0.32 mol) in 1,2-dichloroethane (500 mL) was added oxalyl chloride (48.0 g, 0.38 mol). The reaction mixture was stirred for 24 hours at room temperature. To the reaction mixture was then added pyrrole (22.0 g, 0.33 mol). The reaction mixture was again stirred for 24 hours at room temperature. Aqueous sodium acetate (20%, 200 mL) was added to the reaction mixture and vigorous stirring was continued for 24 hours at room temperature. The organic layer was filtered through a silica gel column and concentrated under reduced pressure to yield 2-benzoylpyrrole which was used without further purification. Yield 43.0 g (80%), mp 76°-77° C.

Workup

  1. stirringThe reaction mixture was again stirred for 24 hours at room temperature
  2. stirringvigorous stirring
  3. waitwas continued for 24 hours at room temperature
  4. filtrationThe organic layer was filtered through a silica gel column
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39334a4537a444a4954079a874d87a18
Source dataset
uspto-grants-1992_01
Patent number
US05082951

Reaction notes

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