Phenyl isocyanate → HCID 20285427, compound

HRID 127597Notes

Reaction equation

HRID 127597 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([CH3:13])=[C:3]1[C:14](=[O:18])[CH2:15][C:16]#[N:17].[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([CH3:13])=[C:3]1[C:14](=[O:18])[CH:15]([C:26](=[O:27])[NH:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]#[N:17]

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 20285422HCID 20285422, compound

Product 1

HCID 20285427HCID 20285427, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

To the solution of 1.6 g of 1,3,5-trimethyl-4-ethoxycarbonyl-β-oxo-2-pyrrolpropionitrile in 30 ml of dry toluene and 0.8 g of anhydrous triethylamine, 0.8 g of phenylisocyanate are added while stirring. The mixture is allowed to stand 10 minues at the steam cone and at room temperature overnight. It is evaporated, the residue taken up in methanol and the solution treated with 2 ml of 5 N hydrochloric acid and 200 ml of water. The crystals formed are collected, washed with water, triturated with methanol-ethanol and recrystallized from methanol, to yield the 1,3,5-trimethyl-4-ethoxycarbonyl-β-oxo-α-phenylcarbamoyl-2-pyrrolpropionitrile melting at 164°-166°.

Workup

  1. customat room temperature
  2. customovernight
  3. customIt is evaporated
  4. additionthe solution treated with 2 ml of 5 N hydrochloric acid and 200 ml of water
  5. customThe crystals formed
  6. customare collected
  7. washwashed with water
  8. customtriturated with methanol-ethanol
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a0adff102e694aa89660de130a9960b8
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

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