4-Chlorobenzoyl chloride → 2-Chloro-1-[4-(4-chlorobenzoyl )-1-methyl-1H-pyrrol-2-yl]-ethanone

HRID 1729182Notes

Reaction equation

HRID 1729182 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[N:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>ClCCCl>[Cl:1][CH2:2][C:3]([C:5]1[N:6]([CH3:10])[CH:7]=[C:8]([C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 25124042-Chloro-1-(1-methyl-1H-pyrrol-2-yl)-ethanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 104941282-Chloro-1-[4-(4-chlorobenzoyl )-1-methyl-1H-pyrrol-2-yl]-ethanoneYield 49.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 30 g (0.19 mole) of 2-chloro-1-(1-methyl-1H-pyrrol-2-yl)-ethanone (10) in 180 mL 1,2-dichloroethane (DCE) under an argon atmosphere was cooled in an ice bath and 60 g AlCl3 (0.45 mole) was added in portions. After stirring for 10 minutes, a solution of 24 mL (0.19 mole) 4-chlorobenzoyl chloride in 110 mL DCE was added dropwise. The ice bath was removed and the reaction was stirred at room temperature overnight. The reaction was poured into 1N HCl/ice and the aqueous layer was extracted three times with methylene chloride. The organics solutions were combined, washed with water, 1N NaOH, water, brine, and dried (MgSO4). Evaporation of the solvent in vacuo gave a solid which was recrystallized from ethyl acetate/methylcyclohexane to give 27.67 g of a solid: mp 130°-132° C.; NMR 300 MHz (CDCl3) d 7.8 (m, 2H); 7.6-7.4 (m, 4H); 4.5 (s, 2H); 4.0 (s, 3H). Anal Calcd for C14H11Cl2NO2 : C, 56.78; H, 3.74; N, 4.73. Found: C, 56.72; H, 3.76; N, 4.73.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction was stirred at room temperature overnight
  3. additionThe reaction was poured into 1N HCl/ice
  4. extractionthe aqueous layer was extracted three times with methylene chloride
  5. washwashed with water, 1N NaOH, water, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent in vacuo
  8. customgave a solid which
  9. customwas recrystallized from ethyl acetate/methylcyclohexane

Sources & evidence

ORD record
ord-5dc45e79e5714b2984dfbf3ef4ba856c
Source dataset
uspto-grants-1994_07
Patent number
US05332736

Reaction notes

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