4-Acetylbenzenesulphonamide → HCID 178419032, Verbindung

HRID 10738

Reaktionsgleichung

Reaktionsgleichung von HRID 10738
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:14]1([C:17]2[NH:18][CH:19]=[C:20]([C:22]3[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=3)[CH:27]=O)[N:21]=2)[CH2:16][CH2:15]1.C[O-].[Li+]>CN(C)C=O>[CH:14]1([C:17]2[NH:18][CH:19]=[C:20]([C:22]3[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26](/[CH:27]=[CH:2]/[C:1]([C:4]4[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=4)=[O:3])[CH:29]=3)[N:21]=2)[CH2:15][CH2:16]1

Komponenten

5

Edukt 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 178418754HCID 178418754, Verbindung

Produkt 1

HCID 178419032HCID 178419032, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.59 mmol) and 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde (Ex-105B, 0.16 g, 0.59 mmol) in N,N-dimethylformamide (16 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The reaction mixture was allowed to stir for 18 hours at ambient temperature. The reaction was quenched with water. The aqueous solution was extracted with dichloromethane. The combined dichloromethane was concentrated. The crude product was purified by flash chromatography. Elution with methanol (10%, v/v, in dichloromethane) gave the title compound as red solid: m.p. 156–160° C. 1H NMR (DMSO-d6) δ 11.65 (bs, 1H), 8.32 (s, 1H), 8.19 (d, J=9.0 Hz, 2H), 8.00 (d, J=15.7 Hz, 1H), 7.95 (d, J=9.0 Hz, 2H), 7.62–7.52 (m, 2H), 7.24 (bs, 1H), 6.73 (s, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 1.98–1.94 (m, 1H), 0.88–0.85 (m 4H). MS m/z=454 ([M+H]+, 100%).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. concentrationThe combined dichloromethane was concentrated
  4. customThe crude product was purified by flash chromatography
  5. washElution with methanol (10%, v/v, in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-bc0bededacff4f5c853c190677c0df9b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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