4-Acetylbenzoic Acid → 4-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzoic acid

HRID 10737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10737
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:13]([N:17]1[CH:21]=[N:20][N:19]=[C:18]1[C:22]1[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=1)[CH:27]=O)[CH:14]([CH3:16])[CH3:15].C[O-].[Li+]>CN(C)C=O>[CH2:13]([N:17]1[CH:21]=[N:20][N:19]=[C:18]1[C:22]1[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26](/[CH:27]=[CH:2]/[C:1]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)=[O:3])[CH:29]=1)[CH:14]([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 114704-Acetylbenzoic AcidHCID 4177230Lithium methanolate2×HCID 219810255-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde

Produkt 1

HCID 103882544-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-acetyl-benzoic acid (0.12 g, 0.75 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.24 g, 0.83 mmol) in N,N-dimethylformamide (6 mL) was added lithium methoxide (1.0M in methanol, 3.0 mL, 3.0 mmol). The solution was allowed to stir overnight and additional lithium methoxide (0.11 g, 2.8 mmol). The reaction was quenched with water after 20 hours. The aqueous solution was washed ethyl acetate, acidified to pH 4. The precipitate was filtered, washed with ethanol and dried in vacuo to afford the title compound as a light yellow solid: m.p.>240° C. (dec.). 1H NMR (DMSO-d6) δ 8.59 (s, 1H), 8.18 (d, J=7.9 Hz, 2H), 8.07 (s, 1H), 8.04–8.01 (m, 3H), 7.85 (d, J=15.7 Hz, 1H), 6.84 (s, 1H), 4.06 (s, 3H), 3.92 (s, 3H), 3.66 (d, J=7.2 Hz, 2H), 1.87–1.74 (m, 1H), 0.72 (d, J=6.7 Hz, 6H). MS m/z=436 ([M+H]+, 100%).

Aufarbeitung

  1. customThe reaction was quenched with water after 20 hours
  2. washThe aqueous solution was washed ethyl acetate
  3. filtrationThe precipitate was filtered
  4. washwashed with ethanol
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b7a1710fbe634762b2d90eac36d3d924
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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