P-Anisidine → 3-[(4-Methoxyphenyl)amino]-1-[2-(methylthio)ethyl]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113767ノート

反応式

HRID 2113767 の反応式
Cl[C:2]1[C:3](=[O:18])[N:4]([CH2:14][CH2:15][S:16][CH3:17])[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:2]2[C:3](=[O:18])[N:4]([CH2:14][CH2:15][S:16][CH3:17])[C:5](=[O:13])[C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:23][CH:22]=1

参加物

4

反応物 2

HCID 7732P-AnisidineHCID 691478763-Chloro-1-[2-(methylsulfanyl)ethyl]-4-phenyl-1H-pyrrole-2,5-dione

生成物 1

HCID 113261143-[(4-Methoxyphenyl)amino]-1-[2-(methylthio)ethyl]-4-phenyl-1H-pyrrole-2,5-dione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

3-Chloro-1-[2-(methylthio)ethyl]-4-phenyl-1H-pyrrole-2,5-dione (0.40 mmol, 113 mg) and 4-methoxyaniline (0.88 mmol, 109 mg) were dissolved in DMF (1 mL). The mixture was heated in a microwave reactor at 150° C. for 10 min. After cooling, the solvent was evaporated under reduced pressure. The residue was partitioned between water and CH2Cl2. The organic phase was evaporated and purified by flash chromatography using a pre-packed silica column. The desired product was eluted with heptane/EtOAc 2:1. Yield 118 mg (80%).1H NMR (400MHz, CDCl3) δ 7.26 (bs, 1H), 7.15-7.06 (m, 3H), 7.01-6.96 (m, 2H), 6.63-6.52 (m, 4H), 3.83 (t, J=7.0 Hz, 2H), 3.69 (s, 3H), 2.79 (t, J=7.0 Hz, 2H), 2.18 (s, 3H).

後処理

  1. temperatureAfter cooling
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was partitioned between water and CH2Cl2
  4. customThe organic phase was evaporated
  5. custompurified by flash chromatography
  6. washThe desired product was eluted with heptane/EtOAc 2:1

出典と根拠

ORDレコード
ord-094ce3114ca847ca81457a1d38c056dd
出典データセット
uspto-grants-2008_10
特許番号
US07432288B2

反応ノート

読み込み中…