Thionyl Chloride → Methyl 3-(4-pentenoylamino)benzoate

HRID 2334

反応式

HRID 2334 の反応式
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1.[C:12](Cl)(=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16].C(O)(=O)CCC=C.S(Cl)(Cl)=O>C(Cl)Cl.N1C=CC=CC=1>[C:12]([NH:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:11])(=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16]

参加物

7

反応物 4

HCID 24386Thionyl ChlorideHCID 611384-Pentenoic acidHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 42284934-Pentenoyl chloride

生成物 1

HCID 10775994Methyl 3-(4-pentenoylamino)benzoate収率 32%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

Methyl(3-amino)benzoate (4.5 g, 29.8 mmol) was taken up in DCM (10 ml) and pyridine (1 ml) at 0° C. 4-Pentenoyl chloride (freshly prepared from 4-pentenoic acid (3.0 g, 29.97 mmol) and thionyl chloride (6.6 ml) at r.t. for 1 h, evaporated and azeotroped with DCM) was added dropwise in DCM (3 ml). The mixture was allowed to warm to r.t. and stirred overnight. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1PS, phase separator), and evaporated. The residue was chromatographed (eluant 30% EtOAc in hexanes) to provide a colourless oil (2.20 g, 32%).

後処理

  1. customat 0° C
  2. customevaporated
  3. customazeotroped with DCM)
  4. additionwas added dropwise in DCM (3 ml)
  5. customThe mixture was evaporated
  6. custompartitioned between EtOAc and 1M HCl
  7. washThe organic portion was washed with 5% KHCO3 and brine
  8. filtrationfiltered (Whatman® 1PS, phase separator)
  9. customevaporated
  10. customThe residue was chromatographed (eluant 30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-21d973d5e9c342b28599ca4532af6af7
出典データセット
uspto-grants-1998_03
特許番号
US05728829

関連ノート

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