Imidazole → N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(3,4-methylenedioxy)phenoxycarbonyl]-thiophene-3-sulfonamide

HRID 1251756

Reaktionsgleichung

Reaktionsgleichung von HRID 1251756
C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:13][C:14]1[C:15]([CH3:32])=[N:16][O:17][C:18]=1[NH:19][S:20]([C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28]([O:30][CH3:31])=[O:29])(=[O:22])=[O:21].[CH2:33]1[O:37][C:36]2[CH:38]=C(O)[CH:40]=[CH:41][C:35]=2[O:34]1.N1C=CN=C1>C1COCC1>[Br:13][C:14]1[C:15]([CH3:32])=[N:16][O:17][C:18]=1[NH:19][S:20]([C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28]([O:30][C:31]1[CH:40]=[CH:41][C:35]2[O:34][CH2:33][O:37][C:36]=2[CH:38]=1)=[O:29])(=[O:21])=[O:22]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 68289SesamolHCID 10833686N-(4-Bromo-3-methyl-5-isoxazolyl)-2-(carbomethoxy)thiophene-3-sulfonamide

Produkt 1

HCID 9826741N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(3,4-methylenedioxy)phenoxycarbonyl]-thiophene-3-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Carbonyidiimidazole (530 mg., 3.26 mmol.) was added to a solution of N-(4-bromo-3-methyl-5-isoxazolyl)-2-carboxylthiophene-3-sulfonamide (Example 17) (1.0 g, 2.72 mmol) in dry THF (10 ml). The mixture was stirred at room temperature for 15 minutes. Sesamol (767 mg., 5.44 mmol) and imidazole (185 mg, 2.72 mmol) were added simultaneously. The resulting mixture was refluxed for 1 hour and allowed to cool to room temperature. The solvent was evaporated. The residue was partitioned between 1N HCl and EtOAc. The organic layer was dried (MgSO4). The solid was filtered and the filtrate concentrated to give a yellow oil which was recrystalized from EtOAc/Et2O/Hexane. N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(3,4-methylenedioxy)phenoxycarbonyl]thiophene-3-sulfonamide was obtained as a white powder (494 mg, 37% yield), m.p. 174-176° C.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. temperatureto cool to room temperature
  3. customThe solvent was evaporated
  4. customThe residue was partitioned between 1N HCl and EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationThe solid was filtered
  7. concentrationthe filtrate concentrated
  8. customto give a yellow oil which
  9. customwas recrystalized from EtOAc/Et2O/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-48665b55742d442e90fd4a9d57aca1c9
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342610B2

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