Hydrochloric Acid → N-(4-Chlorophenoxyethyl)-3-(2-methoxyphenyl)propanamide

HRID 350830

反応式

HRID 350830 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]([OH:13])=O.[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][NH2:22])=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.Cl.Cl>O1CCCC1.C(Cl)Cl>[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][NH:22][C:11](=[O:13])[CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 806523-(o-Methoxyphenyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27941912-(4-Chlorophenoxy)ethylamine

生成物 1

HCID 21055042N-(4-Chlorophenoxyethyl)-3-(2-methoxyphenyl)propanamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-(2-Methoxyphenyl)propionic acid (8.3 g, 46.2 mmol) was dissolved in tetrahydrofuran (20 mL), and 4-chlorophenoxyethylamine (10.3 g, 60.0 mmol) was added dropwise thereto at room temperature. Subsequently, a solution (10 mL) of WSC•HCl (11.5 g, 60.0 mmol) in methylene chloride was slowly added dropwise thereto under ice-cooling, followed by stirring overnight. Under ice cooling, diluted hydrochloric acid was added dropwise thereto, followed by extraction with chloroform. The organic layer was washed with brine, and the resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=20/1), whereby the target compound was obtained (12.8 g, 83%).

後処理

  1. customat room temperature
  2. temperatureunder ice-cooling
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialto drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=20/1), whereby the target compound
  6. customwas obtained (12.8 g, 83%)

出典と根拠

ORDレコード
ord-f87c91c6252b4a1cad701bbfbf389194
出典データセット
uspto-grants-2007_02
特許番号
US07183295B2

関連ノート

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