Phenyl isocyanate → beta-Oxo-alpha-(phenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

HRID 236345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236345
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][C:9]#[N:10])=[O:7].C(N(CC)CC)C.[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>COCCOC>[O:7]=[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)[CH:8]([C:25](=[O:26])[NH:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]#[N:10]

Komponenten

5

Edukt 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 111943553-oxo-3-(1H-pyrrol-2-yl)propanenitrile

Produkt 1

HCID 13370089beta-Oxo-alpha-(phenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 3.1 g of 2-pyrroloylacetonitrile in 25 ml of glyme (ethylene glycol dimethyl ether) and 2.7 g of anhydrous triethylamine is treated with 3.0 g of phenyl isocyanate. After the moderately exothermic reaction, the mixture is let stand overnight. Most of the solvent is evaporated and the residue is treated with water and 12 ml of 10% NaOH solution. The aqueous, alkaline solution is washed with ethyl acetate and acidified with 6N HCl. The product is collected, washed with water, dried and recrystallized from ethanol, to give β-oxo-α-(phenylcarbamoyl)-β-(2-pyrrolyl)-propionitrile, m.p. 207°-209°, the compound of formula II, wherein R1 to R4 are hydrogen.

Aufarbeitung

  1. customAfter the moderately exothermic reaction
  2. customMost of the solvent is evaporated
  3. additionthe residue is treated with water and 12 ml of 10% NaOH solution
  4. washThe aqueous, alkaline solution is washed with ethyl acetate
  5. customThe product is collected
  6. washwashed with water
  7. customdried
  8. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8f0c7c89073d4e649968a6321df8e120
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04644010

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