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

HRID 236345Notes

Reaction equation

HRID 236345 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8f0c7c89073d4e649968a6321df8e120
Source dataset
uspto-grants-1987_02
Patent number
US04644010

Reaction notes

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