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

HRID 2113767Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-094ce3114ca847ca81457a1d38c056dd
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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