Phenyl isocyanate → HCID 20285412, compound

HRID 127596Notes

Reaction equation

HRID 127596 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](=[O:14])[CH2:11][C:12]#[N:13])[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](=[O:14])[CH:11]([C:29](=[O:30])[NH:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]#[N:13])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 20285417HCID 20285417, compound

Product 1

HCID 20285412HCID 20285412, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The solution of 2.5 g of 1-isobutyl-β-oxo-2-pyrrolpropionitrile in 30 ml of toluene and 1.6 g of triethylamine is treated with 1.6 g of phenylisocyanate while stirring. After standing overnight the mixture is filtered and the residue dissolved in 5% aqueous sodium hydroxide. The solution is filtered, acidified with 5 N hydrochloric acid and extracted with diethyl ether-ethyl acetate. The organic solution is washed with water, dried, evaporated, the residue triturated with ethanol and recrystallized from methanol, to give the 1-isobutyl-β-oxo-α-phenylcarbamoyl-2-pyrrolpropionitrile melting at 134°-136°.

Workup

  1. filtrationthe mixture is filtered
  2. dissolutionthe residue dissolved in 5% aqueous sodium hydroxide
  3. filtrationThe solution is filtered
  4. extractionextracted with diethyl ether-ethyl acetate
  5. washThe organic solution is washed with water
  6. customdried
  7. customevaporated
  8. customthe residue triturated with ethanol
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ddcb1eb8fcb74dfb8a7bee2fb4698af3
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

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