2-(4,6-Dimethoxy-2-pyrimidinyloxy)benzaldoxime → O-(3-chlorocinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime

HRID 704297Notes

Reaction equation

HRID 704297 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.[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[CH:25]=[CH:26][CH2:27]Br>CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[CH:25]=[CH:26][CH2:27][O:16][N:15]=[CH:14][C:13]1[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=1[O:11][C:5]1[N:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[N:4]=1

Participants

5

Reactant 2

HCID 9021982-(4,6-Dimethoxy-2-pyrimidinyloxy)benzaldoximeHCID 54032824m-Chlorocinnamyl bromide

Product 1

HCID 54274346O-(3-chlorocinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoximeYield 61.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

5.5 g of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime and 4.6 g of 3-chlorocinnamyl bromide were dissolved in 30 ml of dry acetone containing 2.7 g of anhydrous potassium carbonate. The solution was heated for 5 hours under stirring and reflux. After the reaction mixture was allowed to cool down, the acetone 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 O-(3-chlorocinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime as a semi-solid substance.

Workup

  1. temperatureThe solution was heated for 5 hours
  2. temperaturereflux
  3. temperatureto cool down
  4. distillationthe acetone 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-1291390487a5469d85f51fce06c03e92
Source dataset
uspto-grants-1991_01
Patent number
US04986846

Reaction notes

Loading…