Toluene → HCID 20285418, compound

HRID 127595Notes

Reaction equation

HRID 127595 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](=[O:12])[CH2:9][C:10]#[N:11])[CH3:2].C1(C)C=CC=CC=1.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(N(CC)CC)C>[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](=[O:12])[CH:9]([C:27](=[O:28])[NH:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:10]#[N:11])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7672Phenyl isocyanateHCID 202854201-Ethyl-β-oxo-1H-pyrrole-2-propanenitrile

Product 1

HCID 20285418HCID 20285418, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The mixture of 2.1 g of 1-ethyl-β-oxo-2-pyrrolpropionitrile, 25 ml of toluene and 1.6 g of triethylamine is treated with 1.6 g of phenylisocyanate while stirring. It is allowed to stand overnight at room temperature, evaporated and the residue dissolved in methanol. The solution is poured into 300 ml of water containing 5 ml of 5 N hydrochloric acid and the precipitate is collected. It is dissolved in 5% aqueous sodium hydroxide, the solution filtered, the filtrate re-acidified, the solids collected, washed with water, dried and recrystallized from ethanol, to yield the 1-ethyl-β-oxo-α-phenylcarbamoyl-2-pyrrolpropionitrile melting at 144°-145°.

Workup

  1. customevaporated
  2. dissolutionthe residue dissolved in methanol
  3. additionThe solution is poured into 300 ml of water containing 5 ml of 5 N hydrochloric acid
  4. customthe precipitate is collected
  5. dissolutionIt is dissolved in 5% aqueous sodium hydroxide
  6. filtrationthe solution filtered
  7. customthe filtrate re-acidified, the solids collected
  8. washwashed with water
  9. customdried
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7f0cfd9d05ac4a73ac9ff2e3359f2399
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

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