Water → 1-(2-Methoxyethyl)-3-{[4(methylthio)phenyl]amino}-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113753Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

3-Chloro-1-(2-methoxyethyl)-4-phenyl-1H-pyrrole-2,5-dione (0.26 mmol, 70 mg) and 4-(methylthio)aniline (0.53 mmol, 73 mg) was dissolved in dry CH3CN (2 mL) and the reaction mixture was sequentially subjected to microwave heating single node 140° C. for, 10 min, 140° C. for 10 min, and 140° C. for 20 min. 0.3 mL Water was added and the reaction mixture was purified using HPLC (57% 0.1M ammonium acetate buffer: 43% CH3CN→100% CH3CN, 20 mL/min) to give 49 mg (50%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.22 (bs, 1H), 7.19-7.10 (m, 3H), 7.06-7.00 (m, 2H), 6.95-6.90 (m, 2H), 6.58-6.53 (m, 2H), 3.82 (t, J=5.6 Hz, 2H), 3.63 (t, J=5.6 Hz, 2H), 3.38 (s, 3H), 2.38 (s, 3H).

Workup

customthe reaction mixture was purified

Sources & evidence

ORD record: ord-0dcb2829f5f542a68cddd4809f452c04
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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