Acrylonitrile → HCID 18976205, compound

HRID 2393591Notes

Reaction equation

HRID 2393591 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:5]([NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6].[C:27](#[N:30])[CH:28]=[CH2:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:5]([NH:7][C:8]1([CH2:29][CH2:28][C:27]#[N:30])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 11430Potassium CarbonateHCID 18976182HCID 18976182, compound

Product 1

HCID 18976205HCID 18976205, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under argon atmosphere, a mixture of 2.70 g of 3,4-dichloro-N-(2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl)benzamide, 1.30 g of acrylonitrile, 30 ml of acetone and 1.46 g of potassium carbonate was stirred at room temperature for 1 hour. After removal of solvent, the residue was treated with water and extracted with ethyl acetate. After the ethyl acetate extract was washed and dried, the solvent was removed by evaporation. The residue was crystallized from ethyl acetate-hexane to afford 2.28 g of 3,4-dichloro-N-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]-benzamide as colorless crystals. Melting point: 79° to 84° C., IR (Nujol) (cm-1): 3340, 2325, 1700, 1655, 1610, MS (m/z): 445 & 443 (M+).

Workup

  1. customAfter removal of solvent
  2. additionthe residue was treated with water
  3. extractionextracted with ethyl acetate
  4. extractionAfter the ethyl acetate extract
  5. washwas washed
  6. customdried
  7. customthe solvent was removed by evaporation
  8. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9f49970edd1b4fcdb98718edfd1f1462
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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