Reaktion #10789

ord-a19a657cbf0448f4afbd723ca73bee44

Reaktionsgleichung

COc1cc(OCC(N)=O)c(C=O)cc1-c1cccs1
2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-acetamide
CC(=O)c1ccc(C(=O)O)cc1
4-acetylbenzoic acid
→
COc1cc(OCC(N)=O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1
title compound
Ausbeute 70.0%
COc1cc(OCC(N)=O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1
4-[3E-(2-Carbamoylmethoxy-4-methoxy-5-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid
Ausbeute 70.0%

Edukte

COc1cc(OCC(N)=O)c(C=O)cc1-c1cccs1
2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-acetamide
CC(=O)c1ccc(C(=O)O)cc1
4-acetylbenzoic acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094801B2uspto-grants-2006_08