Phenyl isocyanate → HCID 20285415, compound

HRID 127600Notes

Reaction equation

HRID 127600 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH3:8])=[C:3]1[C:9](=[O:13])[CH2:10][C:11]#[N:12].[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH3:8])=[C:3]1[C:9](=[O:13])[CH:10]([C:21](=[O:22])[NH:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]#[N:12]

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 20285428HCID 20285428, compound

Product 1

HCID 20285415HCID 20285415, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

To the suspension of 1.0 g of 1,3,5-trimethyl-β-oxo-2-pyrrolpropionitrile in 30 ml of dry toluene and 0.7 g of anhydrous triethylamine, 0.75 g of phenylisocyanate are added while stirring. The mixture is warmed for 5 minutes at the steam cone and allowed to stand at room temperature overnight. It is filtered, the residue taken up in methanol and the solution acidified with N hydrochloric acid. The precipitate formed is collected, dissolved in N aqueous sodium hydroxide, re-precipitated with 5 N hydrochloric acid and washed with water, to yield the 1,3,5-trimethyl-β-oxo-α-phenylcarbamoyl-2-pyrrolpropionitrile melting at 172°-174°.

Workup

  1. additionare added
  2. temperatureThe mixture is warmed for 5 minutes at the steam cone
  3. filtrationIt is filtered
  4. customThe precipitate formed
  5. customis collected
  6. dissolutiondissolved in N aqueous sodium hydroxide
  7. customre-precipitated with 5 N hydrochloric acid
  8. washwashed with water

Sources & evidence

ORD record
ord-d7652004d67941929c18b6284206595f
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

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