4-Acetylbenzoic Acid → 4-[3E-(2-Carbamoylmethoxy 4-methoxy-5-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid
Reaction equation
[CH:1]([C:3]1[CH:13]=[C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[C:11]([O:19][CH3:20])=[CH:10][C:4]=1[O:5][CH2:6][C:7]([NH2:9])=[O:8])=O.[C:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)(=[O:23])[CH3:22]>>[C:7]([CH2:6][O:5][C:4]1[CH:10]=[C:11]([O:19][CH3:20])[C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:13][C:3]=1/[CH:1]=[CH:22]/[C:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=[O:23])(=[O:8])[NH2:9]Participants
3
Procedure
The title compound was prepared by condensing 2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-acetamide (Ex-71A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 70% yield, mp 235° C. (dec.). 1H-NMR (300 MHz, DMSO-d6) δ 8.26–8.30 (m, 3H), 8.08–8.11 (m, 4H), 7.67 (d, 1H, J=2.7 Hz), 7.65 (brs, 1H), 7.53 (d, 1H, J=4.0 Hz), 7.49 (brs, 1H), 7.13 (m, 1H), 6.77 (s, 1H), 4.75 (s, 2H), 3.97 (s, 3H). MS (EI) m/z=437 ([M]+, 100%). HRMS (EI) Calcd. for C23H19NO6S: 437.0933. Found: 437.0924.
Sources & evidence
- ORD record
- ord-a19a657cbf0448f4afbd723ca73bee44
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094801B2
Reaction notes
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