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

HRID 704297
노트
인쇄 미리보기

반응식

HRID 704297 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 11430Potassium Carbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1291390487a5469d85f51fce06c03e92
출처 데이터셋
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04986846

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