Potassium Carbonate → HCID 15066852, compound

HRID 466224Notes

Reaction equation

HRID 466224 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.Br[CH2:18][CH2:19][CH2:20][S:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[OH:1][CH2:2][CH2:3][N:4]([CH2:18][CH2:19][CH2:20][S:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15158815HCID 15158815, compoundHCID 198731504-[3-[(2-Hydroxyethyl)amino]propoxy]benzonitrile

Product 1

HCID 15066852HCID 15066852, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-[3-[(2-hydroxyethyl)amino]propoxy]benzonitrile (3 g), 1-bromo-3-(propylthio)propane (2.7 g) and potassium carbonate (3.7 g) in 2-propanol (50 ml) was refluxed for 28 hours. The solvent was evaporated and the residue dissolved in aqueous HCl (2 M) and extracted with diethylether. The aqueous layer was basified with sodium hydroxide (10 M) and extracted with methylene chloride followed by drying over sodium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography. Yield 2.6 g of the title compound as an oil.

Workup

  1. temperaturewas refluxed for 28 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in aqueous HCl (2 M)
  4. extractionextracted with diethylether
  5. extractionextracted with methylene chloride
  6. dry with materialby drying over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d2283751576d46c4bdcb2867fe206004
Source dataset
uspto-grants-1992_10
Patent number
US05155133

Reaction notes

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