Hydrochloric Acid → 2-Chloro-1-[5-(4-nitrobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone

HRID 36861Notes

Reaction equation

HRID 36861 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:12].[Cl:22][CH2:23][C:24](Cl)=[O:25].Cl>ClCCCl>[Cl:22][CH2:23][C:24]([C:9]1[CH:8]=[C:7]([C:11](=[O:12])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[N:6]([CH3:5])[CH:10]=1)=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 2308030(1-Methyl-1H-pyrrol-2-yl)(4-nitrophenyl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 108046192-Chloro-1-[5-(4-nitrobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanoneYield 60.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A 210 g (1.57 mole) sample of AlCl3 was added in portions to a solution of 145.4 g (0.63 mole) of (1 -methyl-1H-pyrrol-2-yl)(4-nitrophenyl)-methanone (1) in 450 mL of 1,2-dichloroethane (DCE). A solution of 125 mL (1.57 mole) of chloroacetyl chloride in 200 mL of DCE was added dropwise. The mixture was stirred 1 h at room temperature. The reaction was poured into 1N HCl and ice, the organics were separated, washed with H2O, 1N NaOH, H2O, brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue was recrystallized from EtOAc/EtOH to give 116.2 g of solid. mp 173°-176° C. Mass spectrum (Cl-CH4) m/z 307 (M+1). NMR (Me2SO-d6)δ 8.4 (d, 2 H); 8.2 (s,1 H); 8.0 (d, 2 H); 7.1 (s, 1 H); 4.8 (s, 2 H); 4.0 (s, 3 H). Anal calcd for C14H11CIN2O4 : Calcd: C, 54.83; H, 3.61; N, 9.13. Found: C, 55.11;H, 3.70; N, 9.10.

Workup

  1. customthe organics were separated
  2. washwashed with H2O, 1N NaOH, H2O, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was recrystallized from EtOAc/EtOH

Sources & evidence

ORD record
ord-b047495e982247fe8d7564994dc59e11
Source dataset
uspto-grants-1995_05
Patent number
US05418236

Reaction notes

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