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

HRID 2334

반응식

HRID 2334 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 10775994Methyl 3-(4-pentenoylamino)benzoate수율 32%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-21d973d5e9c342b28599ca4532af6af7
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728829

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