4-Acetylbenzenesulphonamide → 4-[3E-(2,4-dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonamide

HRID 347369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347369
[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].[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][C:17]=1[CH:18]=O.C[O-].[Li+]>CN(C)C=O.O>[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][C:17]=1/[CH:18]=[CH:2]/[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=1)=[O:3]

Komponenten

6

Edukt 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 210825102,4-Dimethoxy-5-pyrrolidin-1-ylbenzaldehyde

Produkt 1

HCID 694900494-[3E-(2,4-dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ex-48A: To a solution of 4-acetylbenzenesulfonamide (Ex-35A, 0.13 g, 0.64 mmol) and 2,4-dimethoxy-5-pyrrolidin-1-yl-benzaldehyde (Ex-38B, 0.15 g, 0.64 mmol) in N,N-dimethylformamide (5 mL) was added lithium methoxide (1.0 M in methanol, 1.6 mL, 1.6 mmol). The solution was allowed to stir at ambient temperature for 13 h and then at 40° C. for 2 h. HPLC indicated no further change of starting materials. The reaction mixture was then diluted with water, acidified to pH 5. The resulting precipitate was collected by filtration, washed with water, dried in vacuo. The crude product was slurried in ethanol overnight. The solid was collected by filtration, washed with ethanol, dried in vacuo to give 4-[3E-(2,4-dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonamide (0.16 g, 59%) as a red solid, m.p. 220–222° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.22 (d, J=8.7 Hz, 2H), 8.04 (d, J=16.1 Hz, 1H), 7.93 (d, J=8.7 Hz, 2H), 7.64 (d, J=16.1 Hz, 1H), 7.52 (s, 2H), 7.18 (s, 1H), 6.67 (s, 1H), 3.86 (s, 6H), 3.19–3.17 (m, 4H), 1.84–1.83 (m, 4H). HRMS Calcd for C21H24N2O5S: 416.1408 (M+); Found: 416.1408.

Aufarbeitung

  1. waitat 40° C. for 2 h
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo
  5. waitThe crude product was slurried in ethanol overnight
  6. filtrationThe solid was collected by filtration
  7. washwashed with ethanol
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8d711ecda1e64cf9bdaaec9708ec8622
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173129B2

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