Potassium Carbonate → HCID 13362794, compound

HRID 365059Notes

Reaction equation

HRID 365059 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH:18]([CH3:28])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:22]1([NH:21][C:19](=[O:20])[CH:18]([O:14][C:11]2[CH:12]=[CH:13][C:8]([O:7][C:6]3[CH:15]=[CH:16][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[CH:9][CH:10]=2)[CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 991132-Bromo-N-phenylpropanamideHCID 45227124-(4-hydroxyphenoxy)benzonitrile

Product 1

HCID 13362794HCID 13362794, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 30 ml of acetone were added 1.06 g of 4-(4-cyanophenoxy)-phenol, 0.99 g of α-bromopropionanilide and 0.83 g of anhydrous potassium carbonate, and the mixture wask subjected to reflux for 16 hours with stirring. After the reaction mixture was cooled and separated from inorganic salts through filtration, acetone was distilled away therefrom. The residue was purified through a column-chromatography [silica gel, developed with ethyl acetate/n-hexane=1/1(V/V)] to give 1.07 g of the title compound (yield 60%), which was recrystallized from a mixed solvent of benzene-n-hexane to afford a crystal of melting point 133°-134° C.

Workup

  1. temperatureto reflux for 16 hours
  2. temperatureAfter the reaction mixture was cooled
  3. customseparated from inorganic salts through filtration, acetone
  4. distillationwas distilled away
  5. customThe residue was purified through a column-chromatography [silica gel

Sources & evidence

ORD record
ord-69b212377b6e44eb8aa82304a4803d6a
Source dataset
uspto-grants-1986_08
Patent number
US04608081

Reaction notes

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