Hydrochloric Acid → HCID 68831193, compound

HRID 747709Notes

Reaction equation

HRID 747709 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)=[O:7].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29].Cl>CN(C)C=O>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][O:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])=[CH:9][CH:10]=1)#[N:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 177891304-(5-Chloropentanoyl)benzonitrile

Product 1

HCID 68831193HCID 68831193, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

53 mg (0.24 mmol) of 4-(5-chloro-1-oxopentyl)benzonitrile was dissolved in 2 ml of dimethylformamide. 33 mg (0.24 mmol) of potassium carbonate, 40 mg of potassium iodide and 29 mg (0.24 mmol) of 3-hydroxybenzonitrile were added to the solution, and they were stirred at 70° C. overnight. 1 N Hydrochloric acid was added to the reaction mixture. After the extraction with ethyl acetate, the extract was washed with 1 N aqueous sodium hydroxide solution and saturated aqueous common salt solution, and then dried over powdery magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel chromatography to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. washthe extract was washed with 1 N aqueous sodium hydroxide solution and saturated aqueous common salt solution
  3. dry with materialdried over powdery magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by the silica gel chromatography

Sources & evidence

ORD record
ord-2b5e7c2bcbae490aa06a6c5fe28e967c
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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