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

HRID 1775603

反応式

HRID 1775603 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9d507646114648c5bd9f984a4ea6a178
出典データセット
uspto-grants-2016_02
特許番号
US09260448B2

関連ノート

読み込み中…