Methyl trifluoromethyl ketone → 2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 483627Notes

Reaction equation

HRID 483627 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](=O)[CH3:4].[NH2:8][C:9]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:10](Br)[C:11]#[N:12]>C(O)(=O)C.O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:9]2[NH:8][C:3]([C:2]([F:7])([F:6])[F:1])=[CH:4][C:10]=2[C:11]#[N:12])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 9871Methyl trifluoromethyl ketoneHCID 73652954beta-Amino-alpha-bromo-p-chlorocinnamonitrile

Product 1

HCID 110001432-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of trifluoroacetone (3.36 g, 2.7 mL,0.03 mol) in acetic acid is added dropwise at 100° C. to a solution of β-amino-α-bromo-p-chlorocinnamonitrile, (E)- or (Z)- (5.15 g, 0.02 mol) in acetic acid over 41/2 hours. The reaction mixture is heated at 100° C. overnight, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain a gum. The gum is flash chromatographed using silica gel and a 15% ethyl acetate in heptane solution to give the title product as a yellow solid (1.8 g, mp 129°-131° C.) which is identified by 1H and 19FNMR spectral analyses.

Workup

  1. custom2 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto obtain a gum
  7. customchromatographed

Sources & evidence

ORD record
ord-4cacad1365b544dbafd62082bdaa8b20
Source dataset
uspto-grants-1993_07
Patent number
US05225568

Reaction notes

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