2,4,6-Trimethoxyaniline → 2-(4-n-Propylphenylthio)-N-(2,4,6-trimethoxyphenyl)nonanamide

HRID 2257159노트

반응식

HRID 2257159 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:12]([OH:14])=O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH3:22][O:23][C:24]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH3:34])[C:25]=1[NH2:26]>S(Cl)(Cl)=O.C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:12]([NH:26][C:25]2[C:27]([O:33][CH3:34])=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:24]=2[O:23][CH3:22])=[O:14])=[CH:8][CH:9]=1)[CH2:2][CH3:3]

참가 물질

6

반응물 2

HCID 842712,4,6-TrimethoxyanilineHCID 149953862-(4-n-Propylphenylthio)nonanoic acid

생성물 1

HCID 149953872-(4-n-Propylphenylthio)-N-(2,4,6-trimethoxyphenyl)nonanamide수율 49%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

실험 절차

1.54 g (5 mmole) of the title compound of Example 3 in 20 ml of thionyl chloride was refluxed for 3 hours and then concentrated to dryness in vacuo. 523 mg (1.6 mmole) of the resulting acid chloride was dissolved in 20 ml methylene chloride and to the solution was added 292 mg (1.6. mmole) 2,4,6-trimethoxyaniline and 195 mg (1.6 mmole) 4-dimethylaminopyridine. The resulting solution was stirred at room temperature overnight and then concentrated in vacuo. The residue was partitioned between 60 ml ethyl acetate and 20 ml 1N aqueous hydrochloric acid solution. The ethyl acetate layer was washed with 50 ml water and 50 ml saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was chromatographed on 100 g silica gel, eluting with 1:1 hexane/ethyl acetate to yield 370 mg (49% yield) of the title compound as a whitish solid.

후처리

  1. concentrationconcentrated to dryness in vacuo
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between 60 ml ethyl acetate and 20 ml 1N aqueous hydrochloric acid solution
  4. washThe ethyl acetate layer was washed with 50 ml water and 50 ml saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed on 100 g silica gel
  8. washeluting with 1:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-e0ddbdc6002d450d81f01f3cd0be65f6
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05656634

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