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

HRID 344572ノート

反応式

HRID 344572 の反応式
[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][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]

参加物

5

反応物 2

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

生成物 1

HCID 1317170140-(3-Chlorocinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime収率 61.2%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 11430Potassium Carbonate溶媒

実験手順

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 0-(3-chlorocinnamyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime as a semi-solid substance.

後処理

  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)

出典と根拠

ORDレコード
ord-cbef0243e7c7483c80b771fd3ae20117
出典データセット
uspto-grants-1991_10
特許番号
US05053070

反応ノート

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