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

HRID 597874ノート

反応式

HRID 597874 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

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+)

後処理

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

出典と根拠

ORDレコード
ord-24c3727ded9c47f4ac74a8554ca3339a
出典データセット
uspto-grants-2011_03
特許番号
US07897601B2

反応ノート

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