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

HRID 483626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483626
Br[C:2](=[C:5]([NH:13][CH3:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[C:3]#[N:4].[F:15][C:16]([F:21])([F:20])[C:17](=O)[CH3:18]>C(O)(=O)C.O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]2[N:13]([CH3:14])[C:17]([C:16]([F:21])([F:20])[F:15])=[CH:18][C:2]=2[C:3]#[N:4])=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 9871Methyl trifluoromethyl ketoneHCID 85317206HCID 85317206, Verbindung

Produkt 1

HCID 118221892-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of α-bromo-p-chloro-β-(methylamino)cinnamonitrile, (E)- or (Z)- (5.43 g, 0.02 mol) and trifluoroacetone (3.36 g, 2.7 mL, 0.03 mol) in acetic acid is heated at 80° C. for 1-2 hours, 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 (1.7 g, mp 129°-131° C.) which is identified by 1H and 19FNMR spectral analyses.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-24bf63f06e6342c29ea116e72f44bc86
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225568

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