2-(4,6-Dimethoxy-2-pyrimidinyloxy)benzaldoxime → 0-(3-Methylcinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime

HRID 344573Notes

Reaction equation

HRID 344573 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[CH:14]=[N:15][OH:16])[N:4]=1.[CH3:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[CH:25]=[CH:26][CH2:27]Br>C(#N)C.C(=O)([O-])[O-].[K+].[K+]>[CH3:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[CH:25]=[CH:26][CH2:27][C:12]1([O:11][C:5]2[N:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[N:4]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:13]1[CH:14]=[N:15][OH:16]

Participants

5

Reactant 2

HCID 9021982-(4,6-Dimethoxy-2-pyrimidinyloxy)benzaldoximeHCID 53894373m-Methylcinnamyl bromide

Product 1

HCID 1317170150-(3-Methylcinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoximeYield 64.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 11430Potassium CarbonateSolvent

Procedure

5.5 g of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime and 4.2 g of 3-methylcinnamyl bromide were dissolved in 30 ml of acetonitrile containing 2.7 g of anhydrous potassium carbonate, and the solution was heated for 5 hours under stirring and reflux. After the reaction mixture was allowed to cool down, the acetonitrile was distilled out under reduced pressure and the resulting residue was dissolved in 200 ml of ethyl acetate. The ethyl acetate solution was washed with water and the organic layer was dried over anhydrous sodium sulfate. The solution was then concentrated under reduced pressure. The residue was purified by silica gel chromatography (developer: n-hexane:ethyl acetate:4:1) to obtain 5.2 g of 0-(3-methylcinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime as crystals.

Workup

  1. temperaturethe solution was heated for 5 hours
  2. temperaturereflux
  3. temperatureto cool down
  4. distillationthe acetonitrile was distilled out under reduced pressure
  5. dissolutionthe resulting residue was dissolved in 200 ml of ethyl acetate
  6. washThe ethyl acetate solution was washed with water
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. concentrationThe solution was then concentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (developer: n-hexane:ethyl acetate:4:1)

Sources & evidence

ORD record
ord-10c5b5190c6e4ba090ecf60b14b4b11e
Source dataset
uspto-grants-1991_10
Patent number
US05053070

Reaction notes

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