Benzocaine → Ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate

HRID 487525Notes

Reaction equation

HRID 487525 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH2:13]([CH2:17][C:18](=O)[CH3:19])[C:14]([CH3:16])=O>S(=O)(=O)(O)O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:12]=[CH:11][C:9]([N:10]2[C:18]([CH3:19])=[CH:17][CH:13]=[C:14]2[CH3:16])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2337BenzocaineHCID 80352,5-Hexanedione

Product 1

HCID 702059Ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-ethoxycarbonylaniline (82.6 g), acetonylacetone (68.5 g) and concentrated sulfuric acid (one drop) were heated at 150° C. for one hour. The reaction mixture was diluted with ethyl acetate and washed with water, followed by drying and concentrating, whereby 1-(4-ethoxycarbonylphenyl)-2,5-dimethylpyrrole was obtained.

Workup

  1. washwashed with water
  2. customby drying
  3. concentrationconcentrating

Sources & evidence

ORD record
ord-a10ef2ba104c469b8c46bd7bde4a3067
Source dataset
uspto-grants-1994_03
Patent number
US05296344

Reaction notes

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