4-Acetylbenzenesulphonamide → 4-{3E-[2-(Benzotriazol-1-ylmethoxy)-4-methoxy-5-thiophen-2-yl-phenyl]-acryloyl}-benzenesulfonamide

HRID 10742Notes

Reaction equation

[N:1]1([CH2:10][O:11][C:12]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[CH:16][C:13]=2[CH:14]=O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[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]>>[N:1]1([CH2:10][O:11][C:12]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[CH:16][C:13]=2/[CH:14]=[CH:28]/[C:27]([C:30]2[CH:31]=[CH:32][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:34][CH:35]=2)=[O:29])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

Reactant 2

HCID 740654-Acetylbenzenesulphonamide

HCID 219810962-(Benzotriazol-1-ylmethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde

Product 1

HCID 100761374-{3E-[2-(Benzotriazol-1-ylmethoxy)-4-methoxy-5-thiophen-2-yl-phenyl]-acryloyl}-benzenesulfonamideYield 56%

Procedure

The title compound was prepared by condensing 2-(benzotriazol-1-ylmethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-115A) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Light yellow solid, 56% yield, mp 255° C. (dec). 1H-NMR (300 MHz, DMSO-d6) δ 8.21 (s, 1H), 8.09 (d, 3H, J=9.4 Hz), 8.01 (d, 1H, J=7.8 Hz), 7.93 (d, 2H, J=7.8 Hz), 7.75 (d, 2H, J=9.4 Hz), 7.56–7.69 (m, 4H), 7.42–7.47 (m, 1H), 7.38 (s, 1H), 7.13 (dd, 1H, J=5.4, 3.6 Hz), 7.05 (s, 2H), 4.05 (s, 3H). MS (ESI) m/z=547 ([M+H]+, 100%). Anal. Calcd. C27H22N4O5S2: C, 59.33; H, 4.06; N, 10.25; S, 11.73. Found: C, 59.45; H, 4.27; N, 9.92; S, 11.27.

Sources & evidence

ORD record: ord-57d4f5abb36947679528dda35b2d24d2
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094801B2

Reaction notes

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