4-Acetylbenzenesulphonamide → 4-{3E-[2-(1H-Benzoimidazol-2-ylmethoxy)-4-methoxy-5-thiophen-2-yl-phenyl]-acryloyl}-benzenesulfonamide
Reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][C:13]=1[CH:14]=O.[C:27]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1)(=[O:29])[CH3:28]>>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[CH2:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][C:13]=1/[CH:14]=[CH:28]/[C:27]([C:30]1[CH:31]=[CH:32][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:34][CH:35]=1)=[O:29]Participants
3
Procedure
The title compound was prepared by condensing 2-(1H-benzoimidazol-2-ylmethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-113A) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Light orange solid, 56% yield, mp 235–237° C. (dec). 1H-NMR (300 MHz, DMSO-d6) δ 8.27 (s, 1H), 8.19 (d, 2H, J=8.4 Hz), 8.11 (d, 1H, J=15.4 Hz), 7.98 (d, 1H, J=15.4 Hz), 7.89 (d, 2H, J=8.4 Hz), 7.66–7.70 (m, 3H), 7.53–7.55 (m, 3H), 7.22–7.27 (m, 2H), 7.12–7.15 (m, 2H), 5.59 (s, 2H), 4.01 (s, 3H). MS (ESI) m/z=546 ([M+H]+, 100%). Anal. Calcd. for C28H23N3O5S2: C, 61.64; H, 4.25; N, 7.70; S, 11.75. Found: C, 61.49; H, 4.47; N, 7.74; S, 11.58.
Sources & evidence
- ORD record
- ord-cbd9458b4edf41a1a9c88fbbd2080d53
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094801B2
Reaction notes
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