4-Acetylbenzenesulphonamide → 4-{3E-[4-(3-Hydroxy-2-hydroxymethyl-propoxy)-2-methoxy-5-thiophen-2-yl-phenyl]-acryloyl}-benzenesulfonamide

HRID 10730Notes

Reaction equation

[OH:1][CH2:2][CH:3]([CH2:21][OH:22])[CH2:4][O:5][C:6]1[C:13]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:12][C:9]([CH:10]=O)=[C:8]([O:19][CH3:20])[CH:7]=1.[C:23]([C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1)(=[O:25])[CH3:24]>>[OH:1][CH2:2][CH:3]([CH2:21][OH:22])[CH2:4][O:5][C:6]1[C:13]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:12][C:9](/[CH:10]=[CH:24]/[C:23]([C:26]2[CH:27]=[CH:28][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)=[O:25])=[C:8]([O:19][CH3:20])[CH:7]=1

Participants

Reactant 2

HCID 740654-Acetylbenzenesulphonamide

HCID 161159124-(3-Hydroxy-2-hydroxymethyl-propoxy)-2-methoxy-5-thiophen-2-yl-benzaldehyde

Product 1

HCID 104137684-{3E-[4-(3-Hydroxy-2-hydroxymethyl-propoxy)-2-methoxy-5-thiophen-2-yl-phenyl]-acryloyl}-benzenesulfonamideYield 72%

Procedure

The title compound was prepared by condensing 4-(3-hydroxy-2-hydroxymethyl-propoxy)-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-50C) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Yellow solid, 72% yield, mp 191–192° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.29–8.32 (m, 3H), 8.09 (d, 1H, J=16.0 Hz), 7.99 (d, 2H, J=8.1 Hz), 7.92 (d, 1H, J=16.0 Hz), 7.70 (d, 1H, J=3.3 Hz), 7.53–7.56 (m, 3H), 7.14 (dd, 1H, J=5.4, 3.3 Hz), 6.87 (s, 1H), 4.61 (t, 2H, J=5.1 Hz), 4.28 (d, 2H, J=5.1 Hz), 4.00 (s, 3H), 3.60–3.67 (m, 4H), 2.11–2.15 (m, 1H). MS (ESI) m/z=504 ([M+H]+, 100%). Anal. Calcd. for C24H25NO7S2.½H2O: C, 56.23; H, 5.11; N, 2.73; S, 12.51. Found: C, 56.32; H, 5.06; N, 2.83; S, 12.55.

Sources & evidence

ORD record: ord-e886c98fe08c445a918a83a5ccce6da2
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094801B2

Reaction notes

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