Benzoyl chloride → HCID 21915560, compound

HRID 1368427Notes

Reaction equation

HRID 1368427 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15]1[CH:19]=[C:18]([CH3:20])[NH:17][C:16]=1[C:21]([O:23]CC)=[O:22]>ClC(Cl)C>[C:1]([C:19]1[C:15]([CH3:14])=[C:16]([C:21]([OH:23])=[O:22])[NH:17][C:18]=1[CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21915560HCID 21915560, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of benzoyl chloride (1 equiv.) and aluminum chloride (1 equiv.) in dichloroethane at 0° C. was added ethyl 3,5-dimethyl-2-pyrrolecarboxylate (1 equiv.). The mixture was stirred at 80° C. for 4 hr. The mixture was then extracted with ethyl acetate (EtOAc) and H2O. The combined organic extracts were washed with saturated sodium bicarbonate and brine, dried and concentrated to give (51%) of 4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (EtOAc) and H2O
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-44d5371e99034ea3a8284317188bd9bf
Source dataset
uspto-grants-2003_06
Patent number
US06573293B2

Reaction notes

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