Methyl Acrylate → Methyl 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate

HRID 429996Notes

Reaction equation

HRID 429996 reaction equation
Cl[CH:2]([N:7]=[C:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3]([F:6])([F:5])[F:4].[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].N12CCCN=C1CCCCC2>CN(C)C=O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[NH:7][C:2]([C:3]([F:6])([F:5])[F:4])=[CH:19][C:18]=2[C:17]([O:21][CH3:22])=[O:20])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 72751476N-[1-chloro-(2,2,2-trifluoroethyl)]-4-chlorobenzimidoyl chloride

Product 1

HCID 11034029Methyl 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylateYield 26.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-[1-chloro-(2,2,2-trifluoroethyl)]-4-chlorobenzimidoyl chloride (3.40 g, 0.012 mol) and methyl acrylate (1.26 g, 0.015 mol) in N,N-dimethylformamide (10 mL) is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 5.0 g, 0.033 mol) over 1 hour. The reaction mixture is then held at 600° C. for 15 minutes, quenched with dilute HCl, and extracted with ethyl acetate. The organic extract is concentrated in vacuo to obtain a residue. Flash chromatography of the residue on silica gel, packed and eluted with 20% ethyl acetate in heptane, and crystallization from heptane gives the title product as a yellow solid (0.95 g, 26.0% yield) which is identified by 1H and 19F NMR spectral analyses.

Workup

  1. customquenched with dilute HCl
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. concentrationis concentrated in vacuo
  5. customto obtain a residue
  6. washeluted with 20% ethyl acetate in heptane, and crystallization from heptane

Sources & evidence

ORD record
ord-b9a518ec9f334d659a6d6060db119d75
Source dataset
uspto-grants-2001_11
Patent number
US06320059B1

Reaction notes

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