Chloroacetyl chloride → 2-Chloro-1-[5-(2,4-Dichlorobenzoyl)-1,2,4-trimethyl-1H-pyrrol-3-yl]-ethanone

HRID 841033Notes

Reaction equation

HRID 841033 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[N:12]([CH3:18])[C:13]([CH3:17])=[CH:14][C:15]=1[CH3:16])=[O:10].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:23][CH2:24][C:25](Cl)=[O:26]>ClCCCl>[Cl:23][CH2:24][C:25]([C:14]1[C:15]([CH3:16])=[C:11]([C:9](=[O:10])[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:12]([CH3:18])[C:13]=1[CH3:17])=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15517718(2,4-Dichlorophenyl)(1,3,5-trimethyl-1H-pyrrol-2-yl)-methanone

Product 1

HCID 107371392-Chloro-1-[5-(2,4-Dichlorobenzoyl)-1,2,4-trimethyl-1H-pyrrol-3-yl]-ethanoneYield 87.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 48.65 g (0.17 mole) of (2,4-dichlorophenyl)(1,3,5-trimethyl-1H-pyrrol-2-yl)-methanone (5) in 480 mL 1,2-dichloroethane was cooled in an ice bath and 53.5 g (0.425 mole) of AlCl3 was added in four portions. A 33.5 mL portion of (0.425 mole) chloroacetyl chloride was added dropwise. The ice bath was removed and the reaction allowed to stir for 3h under argon. A 10 g sample of AlCl3 was added and the reaction was stirred overnight. The mixture was poured into 1N HCl/ice and the organic layer was separated. The aqueous layer was extracted twice with methylene chloride. The organics were combined and washed with water, NaHCO3, water, brine, and dried (MgSO4). The solvent was evaporated in vacuo and the residue recrystallized from methylcyclohexane to give 53.50 g of product: mp 100-102° C.; mass spectrum (Cl—CH4) m/z=358 (M+1); NMR 300 MHz (CDCl3) d 7.55 (s, 1 H); 7.4 (s, 2 H); 4.4 (s, 2 H); 3.7 (s, 3 H); 2.5 (s, 3 H); 1.9 (s, 3 H). Anal Calcd for C16H14NO2: C, 53.58; H, 3.93; N, 3.91. Found: C, 53.48; H, 3.81; N, 3.93.

Workup

  1. customThe ice bath was removed
  2. additionA 10 g sample of AlCl3 was added
  3. stirringthe reaction was stirred overnight
  4. additionThe mixture was poured into 1N HCl/ice
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted twice with methylene chloride
  7. washwashed with water, NaHCO3, water, brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated in vacuo
  10. customthe residue recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-7d951794a3cf44c9b84ffd78c4b8a11c
Source dataset
uspto-grants-2002_04
Patent number
US06369228B2

Reaction notes

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