P-Anisidine → 3-Amino-N-(4-methoxyphenyl)-4-phenylthiophene-2-carboxamide

HRID 1775603

반응식

HRID 1775603 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C[Al](C)C.[NH2:14][C:15]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][S:17][C:16]=1[C:26](OC)=[O:27]>C1(C)C=CC=CC=1>[NH2:14][C:15]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][S:17][C:16]=1[C:26]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:27]

참가 물질

5

반응물 3

HCID 7732P-AnisidineHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 16682925Trimethylaluminum

생성물 1

HCID 867298003-Amino-N-(4-methoxyphenyl)-4-phenylthiophene-2-carboxamide수율 85.7%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

p-Anisidine (29 mg, 0.24 mmol) was dissolved in toluene (2 ml) in a reaction vessel, and trimethylaluminum (2 M in TIIF, 0.12 ml) was added thereto at 0° C. After stirring for 10 min, to the mixture was added methyl 3-amino-4-phenylthiophene-2-carboxylate (50 mg, 0.21 mmol). The resulting mixture was heated to reflux at 120° C. for 16 hr. The completion of the reaction was confirmed by TLC. The reaction mixture was allowed to cool to room temperature, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (hexane:EtOAc=5:1) to give (57 mg, 0.18 mmol, 84% yield) of the title compound.

후처리

  1. customat 0° C
  2. temperatureThe resulting mixture was heated
  3. temperatureto cool to room temperature
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate was purified by silica gel column chromatography (hexane:EtOAc=5:1)

출처 및 근거

ORD 기록
ord-9d507646114648c5bd9f984a4ea6a178
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260448B2

연결된 노트

불러오는 중…