Toluene → HCID 20285410, compound

HRID 127602Notes

Reaction equation

HRID 127602 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([C:8](=[O:12])[CH2:9][C:10]#[N:11])=[C:3]1[CH3:13].C1(C)C=CC=CC=1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(N(CC)CC)C>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([C:8](=[O:12])[CH:9]([C:28](=[O:29])[NH:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]#[N:11])=[C:3]1[CH3:13]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7672Phenyl isocyanateHCID 12607122HCID 12607122, compound

Product 1

HCID 20285410HCID 20285410, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The suspension of 1.0 g of 1,2,5-trimethyl-β-oxo-3-pyrrolpropionitrile, 40 ml of toluene and 0.7 g of triethylamine is treated with 0.75 g of phenylisocyanate and warmed for 5 minutes on the steam cone until all is dissolved. After standing overnight, the precipitate formed is collected, taken up in methanol, and the solution added to the mixture of 3 ml of 5 N hydrochloric acid and 250 ml of water. The crude product formed is collected, washed with water, dissolved in 5% aqueous sodium hydroxide, filtered, and the alkaline filtrate acidified with 5 N hydrochloric acid. The precipitate is collected, washed with water, air-dried and recrystallized from ethanol, to yield the 1,2,5-trimethyl-β-oxo-α-phenylcarbamoyl-3-pyrrolpropionitrile melting at 158°-160°.

Workup

  1. temperaturewarmed for 5 minutes on the steam cone until
  2. dissolutionall is dissolved
  3. customthe precipitate formed
  4. customis collected
  5. additionthe solution added to the mixture of 3 ml of 5 N hydrochloric acid and 250 ml of water
  6. customThe crude product formed
  7. customis collected
  8. washwashed with water
  9. dissolutiondissolved in 5% aqueous sodium hydroxide
  10. filtrationfiltered
  11. customThe precipitate is collected
  12. washwashed with water
  13. customair-dried
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6f00d3033d3645a696bfbbe800260853
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

Loading…