Water → 1-[4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]methanesulfonamide

HRID 583911Notes

Reaction equation

[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH3:16])=[C:6]([C:17](O)=[O:18])[C:5]=1[C:20](O)=[O:21])[CH3:2].[NH2:23][C:24]1[CH:34]=[CH:33][C:27]([CH2:28][S:29]([NH2:32])(=[O:31])=[O:30])=[CH:26][CH:25]=1.O>C(O)(=O)C>[CH2:15]([O:14][C:7]1[C:6]2[C:17](=[O:18])[N:23]([C:24]3[CH:34]=[CH:33][C:27]([CH2:28][S:29]([NH2:32])(=[O:30])=[O:31])=[CH:26][CH:25]=3)[C:20](=[O:21])[C:5]=2[C:4]([O:3][CH2:1][CH3:2])=[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12)[CH3:16]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1,4-diethoxy-2,3-naphthalenedicarboxylic acid (0.75 g, 2.5 mmol, 1.1 eqs) in glacial acetic acid (5 ml) was added 4-amino-benzylsulfonamide (0.43 g, 2.3 mmol). The reaction mixture was heated at 120° C. for 18 h. The reaction mixture was allowed to cool to ambient temperature and then poured into water (5 ml). The precipitate was filtered off, triturated with ethyl acetate/40:60 petroleum ether and then dried in vacuo to give the title compound as a beige solid (790 mg, 69%). δH [2H6]—DMSO 1.48 (6H, t); 4.40 (2H, s); 4.52 (4H, q); 7.00 (2H, s); 7.51 (2H, d, 8.5Hz); 7.56 (2H, d, 8.5 Hz); 7.89 (2H, m); 8.43 (2H, m)

Workup

temperatureto cool to ambient temperature
filtrationThe precipitate was filtered off
customtriturated with ethyl acetate/40:60 petroleum ether
customdried in vacuo

Sources & evidence

ORD record: ord-eef0306e3ff440d68fd2da3879df7cfb
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924297B2

Reaction notes

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