Potassium Carbonate → HCID 18976214, compound

HRID 2393594Notes

Reaction equation

HRID 2393594 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17])=[O:6].[C:29]1([CH2:35][CH2:36][CH2:37]Br)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:37][CH2:36][CH2:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:9]1=[O:17])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 18976195HCID 18976195, compound

Product 1

HCID 18976214HCID 18976214, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.06 g of ethyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-2-oxo-1H-indol-3-yl]propionate, 1.0 g of 3-phenylpropyl bromide, 1.10 g of potassium carbonate and 16 ml of acetone was refluxed overnight. The solvent was removed by evaporation. The residue was extracted with ethyl acetate, washed with water and dried. After removal of solvent, the residual solid was crystallized from isopropyl ether-hexane to afford 1.25 g of ethyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-2-oxo-1-(3-phenylpropyl)-1H-indol-3-yl]propionate as a colorless solid. Melting point: 119.5° to 121.5° C., IR (Nujol) (cm-1): 3320, 1730, 1700, 1660, 1615, FAB-MS (m/z): 541 & 539 (MH+).

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed by evaporation
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customAfter removal of solvent
  7. customthe residual solid was crystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-9edca11313774797a9e555c162b1c510
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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