HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → 1-Methyl-beta-oxo-alpha-(p-methoxyphenylcarbamoyl)-2-pyrrolpropionitrile

HRID 127593
Notes
Print preview

Reaction equation

HRID 127593 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:11])[CH2:8][C:9]#[N:10].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:11])[CH:8]([C:28](=[O:29])[NH:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=1)[C:9]#[N:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 794431-Isocyanato-4-methoxybenzeneHCID 27771703-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile

Product 1

HCID 145557041-Methyl-beta-oxo-alpha-(p-methoxyphenylcarbamoyl)-2-pyrrolpropionitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The suspension of 2.0 g of the 1-methyl-β-oxo-2-pyrrolpropionitrile in 50 ml of toluene and 1.6 g of triethylamine is treated with 2.1 g of p-methoxyphenylisocyanate. The mixture is warmed gently until all is dissolved and allowed to stand overnight at room temperature. It is evaporated, the residue is taken up in methanol and combined with 10 ml of 10% aqueous sodium hydroxide and 250 ml of water. The alkaline solution is filtered, acidified with 5 N hydrochloric acid and the precipitate formed collected. It is washed with water, dried, triturated with warm methanol-ethyl acetate, and recrystallized from ethyl acetate, to yield the 1-methyl-β-oxo-α-(p-methoxyphenylcarbamoyl)-2-pyrrolpropionitrile melting at 192°-193°.

Workup

  1. temperatureThe mixture is warmed gently until
  2. dissolutionall is dissolved
  3. customIt is evaporated
  4. filtrationThe alkaline solution is filtered
  5. customthe precipitate formed
  6. customcollected
  7. washIt is washed with water
  8. customdried
  9. customtriturated with warm methanol-ethyl acetate
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bd67a2403f5947ea99ebdfd823a2528c
Source dataset
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04256759

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes