Benzoyl chloride, 3-nitro- → HCID 14500623, compound

HRID 1761580Notes

Reaction equation

HRID 1761580 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][CH3:11])[CH2:2][CH2:3][CH3:4].[N+:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19])([O-:14])=[O:13]>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:6]([CH2:10][CH3:11])=[CH:7][CH:8]=[C:9]1[C:18](=[O:19])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 14500622HCID 14500622, compound

Product 1

HCID 14500623HCID 14500623, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 19 g (160 mmol) of 1-butyl-2-ethylpyrrole in 300 ml of toluene was treated with 38 g (200 mmol) of m-nitrobenzoyl chloride. The reaction mixture was refluxed under nitrogen atmosphere for 18 hours, cooled and purified by column chromatography on 1 Kg of deactivated alumina (containing 3% water), using hexane-acetone (90:10) as eluant. There were obtained 13.2 g (35%) of 1-butyl-2-(3'-nitrobenzoyl)-5-ethylpyrrole, the title compound, as an oil.

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 18 hours
  2. temperaturecooled
  3. custompurified by column chromatography on 1 Kg of deactivated alumina (containing 3% water)

Sources & evidence

ORD record
ord-7ecc84efea44458e99ce800abb82ed2f
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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