Potassium Carbonate → HCID 14995285, compound

HRID 2248901Notes

Reaction equation

HRID 2248901 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:27]([C:29]1[O:30][C:31]2[CH:37]=[C:36]([CH2:38]Br)[CH:35]=[CH:34][C:32]=2[N:33]=1)#[N:28]>CC(C)=O.CN(C)C=O>[C:27]([C:29]1[O:30][C:31]2[CH:37]=[C:36]([CH2:38][O:20][C:16]3[CH:17]=[CH:18][CH:19]=[C:14](/[CH:13]=[CH:12]/[C:8]4[CH:7]=[CH:6][C:5]5[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=5)[N:9]=4)[CH:15]=3)[CH:35]=[CH:34][C:32]=2[N:33]=1)#[N:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10107780HCID 10107780, compoundHCID 19994737HCID 19994737, compound

Product 1

HCID 14995285HCID 14995285, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the (E)-3-(7-chloro-2quinolinylethenyl)phenol (1.485 g, 5.28 mmol) in acetone (120 ml) and dimethylformamide (I5 ml) at room temperature are added successively potassium carbonate (1.09 g, 7.0 mmol) and 2-cyano-6-(bromomethyl)benzoxazole (1.25 g, 5.27 mmol). The resulting solution-suspension is refluxed for 16 hours and concentrated. Water (100 ml) and ethyl acetate (150 ml) are added. Extraction with ethyl acetate is followed by washing with water and brine, drying (MgSO4) and evaporation under reduced pressure. The residue is subjected to flash chromatography over silica gel. Elution is with 33% ethyl acetate in hexane and concentration of the appropriate fractions provides (E)-2-cyano-6-[3-(7-chloro-2-quinolinylethenyl) phenoxymethyl]-benzoxazole.

Workup

  1. temperatureThe resulting solution-suspension is refluxed for 16 hours
  2. concentrationconcentrated
  3. additionWater (100 ml) and ethyl acetate (150 ml) are added
  4. extractionExtraction with ethyl acetate
  5. washby washing with water and brine
  6. customdrying
  7. custom(MgSO4) and evaporation under reduced pressure
  8. washElution

Sources & evidence

ORD record
ord-b7252a368b3d465bb6eacfc8f32a12ab
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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