2-[(4-Acetylphenyl)sulfanyl]acetic acid → {4-[(E)-3-(5-Benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-phenylsulfanyl}-acetic acid

HRID 10631Notes

Reaction equation

HRID 10631 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[S:15]1[C:19]([C:20]2[C:21]([O:30][CH3:31])=[CH:22][C:23]([O:28][CH3:29])=[C:24]([CH:27]=2)[CH:25]=O)=[CH:18][C:17]2[CH:32]=[CH:33][CH:34]=[CH:35][C:16]1=2>>[S:15]1[C:19]([C:20]2[C:21]([O:30][CH3:31])=[CH:22][C:23]([O:28][CH3:29])=[C:24](/[CH:25]=[CH:2]/[C:1]([C:4]3[CH:5]=[CH:6][C:7]([S:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:9]=3)=[O:3])[CH:27]=2)=[CH:18][C:17]2[CH:32]=[CH:33][CH:34]=[CH:35][C:16]1=2

Participants

3

Reactant 2

HCID 144040822-[(4-Acetylphenyl)sulfanyl]acetic acidHCID 161159165-Benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde

Product 1

HCID 21041603{4-[(E)-3-(5-Benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-phenylsulfanyl}-acetic acid

Procedure

The title compound was prepared by condensing (4-acetylphenylthio)acetic acid (Ex-23B) and 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde (Ex-3A) in a similar manner as described in Ex-22. Yellow solid, mp 136–138° C. (dec.). 1H-NMR (DMSO-d6) δ 8.35 (s, 1H), 8.08 (d, J=7.4 Hz, 2H), 8.03 (d, J=16.3 Hz, 1H), 7.93–7.87 (m, 3H), 7.82 (d, J=7.0 Hz, 1H), 7.42 (d, J=7.9 Hz, 2H), 7.37–7.27 (m, 2H), 6.85 (s, 1H), 4.02 (s, 3H), 3.99 (s, 3H), 3.93 (s, 2H). MS m/z=491 ([M+H]+, 100%).

Sources & evidence

ORD record
ord-6dfae3c96f5446508413bd94bf9d0b34
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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