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Dimethyl malonate → Dimethyl 2-(3'-{[methyl-(1-phenylmethanoyl)-amino] methyl}biphenyl-4-ylmethylene)malonate

HRID 584915
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반응식

HRID 584915 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:25])[C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)=[CH:5][CH:4]=1)=O.[C:26]([O:33][CH3:34])(=[O:32])[CH2:27][C:28]([O:30][CH3:31])=[O:29].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:25][N:16]([CH2:15][C:11]1[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[C:27]([C:26]([O:33][CH3:34])=[O:32])[C:28]([O:30][CH3:31])=[O:29])=[CH:8][CH:7]=2)[CH:14]=[CH:13][CH:12]=1)[C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7943Dimethyl malonateHCID 9793820Piperidine, acetateHCID 22341491N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamide

생성물 1

HCID 22341500Dimethyl 2-(3'-{[methyl-(1-phenylmethanoyl)-amino] methyl}biphenyl-4-ylmethylene)malonate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

1.54 g (4.25 mmol) of N-(4′-formylbiphenyl-3-ylmethyl)-N-methylbenzamide (prepared as in Example 1(e)), 20 ml of toluene, 0.56 g (4.25 mmol)) of dimethyl malonate and 123 mg (0.85 mmol) of piperidine acetate are introduced into a three-necked flask under a stream of nitrogen. The mixture is refluxed for 5 hours, while separating off the water formed using Dean-Stark apparatus. The reaction medium is cooled, extracted with ethyl acetate and washed with water. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The crude product is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30). After evaporation of the solvents, 1.4 g (75%) of the expected product are collected.

후처리

  1. temperatureThe mixture is refluxed for 5 hours
  2. customwhile separating off the water
  3. customformed
  4. temperatureThe reaction medium is cooled
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. customThe organic phase is separated out
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe crude product is purified by chromatography on a column of silica
  11. washeluted with a mixture of heptane and ethyl acetate (70/30)
  12. customAfter evaporation of the solvents, 1.4 g (75%) of the expected product
  13. customare collected

출처 및 근거

ORD 기록
ord-d5e90e8e9ae9433ca134dcaddb8ee651
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06927228B2

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