Triethylamine → beta-Oxo-alpha-(3-pyridylcarbamoyl)-beta-(1-methyl-2-pyrrolyl)propionitrile

HRID 1903100Notes

Reaction equation

HRID 1903100 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.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N:25]=[C:26]=[O:27])[CH:20]=1>C1(C)C=CC=CC=1>[O:11]=[C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)[CH:8]([C:26](=[O:27])[NH:25][C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27604933-IsocyanatopyridineHCID 27771703-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile

Product 1

HCID 86739305beta-Oxo-alpha-(3-pyridylcarbamoyl)-beta-(1-methyl-2-pyrrolyl)propionitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the suspension of 12.9 g of 1-methyl-β-oxo-2-pyrrolepropionitrile (U.S. Pat. No. 4,256,759) in 150 ml of dry toluene and 10.1 g of anhydrous triethylamine are added 10.8 g of 3-pyridyl isocyanate while stirring. After all solids are dissolved, the solution is allowed to stand at room temperature overnight. The mixture is evaporated to dryness, the residue taken up in methanol and the solution is neutralized to pH ca. 6 with 3 N hydrochloric acid and diluted with 600 ml of water. The resulting precipitate is collected, washed with water, and dried to yield the β-oxo-α-(3-pyridylcarbamoyl)-β-(1-methyl-2-pyrrolyl)propionitrile.

Workup

  1. dissolutionAfter all solids are dissolved
  2. customThe mixture is evaporated to dryness
  3. additiondiluted with 600 ml of water
  4. customThe resulting precipitate is collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f707f20d2ce2441a9ac3e8795478da11
Source dataset
uspto-grants-1984_03
Patent number
US04435407

Reaction notes

Loading…