Methanol → 5-(2,4-Dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-amide

HRID 597874노트

반응식

HRID 597874 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][CH:11]=[CH:12][C:13](Cl)=[O:14].CCN(CC)CC.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[CH:31][CH2:32][NH2:33])=[CH:26][CH:25]=1.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([CH:30]=[CH:31][CH2:32][NH:33][C:13](=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:28][CH:29]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 8471TriethylamineHCID 536960003-(4-Chlorophenyl)allylamineHCID 724729475-(2,4-Dichloro-phenyl)-penta-2,4-dienoyl chloride

생성물 1

HCID 724730935-(2,4-Dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-amide수율 100.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 5-(2,4-dichloro-phenyl)-penta-2,4-dienoyl chloride (62.5 mmol) in 300 mL CH2Cl2 at 0° C. was added Et3N (13.0 mL) followed by DMAP (i.e., 4-diaminomethylpyridine) (760 mg). To this was added a solution of 3-(4-chloro-phenyl)-allylamine (10.5 g) in 30 mL CH2Cl2. The mixture was stirred at 0° C. for 1 hr. Then 2 mL of MeOH was added, and the solution was stirred for 10 min. The solution was then diluted with aq. NaHCO3 and extracted with EtOAc. Filtration of solids and concentration of EtOAc layers provided a combined yield of 24.6 g of 5-(2,4-dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-amide. MS: m/e 392.2 (MH+)

후처리

  1. stirringthe solution was stirred for 10 min
  2. extractionextracted with EtOAc
  3. filtrationFiltration of solids and concentration of EtOAc layers

출처 및 근거

ORD 기록
ord-24c3727ded9c47f4ac74a8554ca3339a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897601B2

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