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

HRID 2113767노트

반응식

HRID 2113767 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-094ce3114ca847ca81457a1d38c056dd
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432288B2

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