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

HRID 1358786Notes

Reaction equation

HRID 1358786 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 60° 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-f23f5f8ef40d4e5baf10e86b10e58473
Source dataset
uspto-grants-2003_07
Patent number
US06596902B2

Reaction notes

Loading…