Acetamide, 2-cyano-N-phenyl- → Prinomide

HRID 127589

Reaktionsgleichung

Reaktionsgleichung von HRID 127589
[C:1]1([NH:7][C:8]([CH2:10][C:11]#[N:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH3:19][N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26]>CN(C)C=O>[CH3:19][N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](=[O:26])[CH:10]([C:8](=[O:9])[NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11]#[N:12]

Komponenten

5

Edukt 3

HCID 69296Acetamide, 2-cyano-N-phenyl-HCID 27950921-Methyl-1H-pyrrole-2-carbonyl chlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 60352Prinomide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the solution of 4.0 g of phenylcarbamoyl-acetonitrile in 50 ml of dimethylformamide 28 g of potassium tert. butoxide are added while stirring under nitrogen. After 2 hours the resulting suspension is cooled to 5° and 4.0 g of 1-methylpyrrol-2-carboxylic acid chloride (U.S. Pat. No. 3,551,571) are added during 10 minutes. The mixture is stirred for 18 hours at room temperature, poured into 300 ml of ice water and the precipitate formed filtered off. It is washed with water, dried and recrystallized from ethanol, to yield the 1-methyl-β-oxo-α-phenylcarbamoyl-2-pyrrolpropionitrile melting at 172°-174°; it is identical with that obtained according to Example 1.

Aufarbeitung

  1. temperatureAfter 2 hours the resulting suspension is cooled to 5°
  2. addition3,551,571) are added during 10 minutes
  3. stirringThe mixture is stirred for 18 hours at room temperature
  4. customthe precipitate formed
  5. filtrationfiltered off
  6. washIt is washed with water
  7. customdried
  8. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b1750a43d37a4d2da5eb70559411b709
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256759

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