2-Methylbenzenesulfonamide → 4-Tert-butyl-2-{5-[2-(2-methylbenzenesulfonamidocarbonyl)phenylmethoxy]benzofuran-2-yl}thiazole

HRID 487686

Reaktionsgleichung

Reaktionsgleichung von HRID 487686
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27](O)=[O:28])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37]([NH2:40])(=[O:39])=[O:38].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([NH:40][S:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[CH3:30])(=[O:38])=[O:39])=[O:28])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 190927584-Tert-butyl-2-[5-(2-carboxyphenylmethoxy)benzofuran-2-yl]thiazole

Produkt 1

HCID 190928024-Tert-butyl-2-{5-[2-(2-methylbenzenesulfonamidocarbonyl)phenylmethoxy]benzofuran-2-yl}thiazoleAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-tert-butyl-2-[5-(2-carboxyphenylmethoxy)benzofuran-2-yl]thiazole (0.2 g), 2-methylbenzenesulfonamide (0.11 g), 4-dimethylaminopyridine (0.12 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.19 g) in N,N-dimethylformamide (10 ml) was stirred at ambient temperature for 1 day. The resulting mixture was poured into ice-water. The resulting precipitates were collected by filtration and washed with water. The crude compound was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (40:1). The fractions containing object compound were combined and concentrated under reduced pressure to give an oil. The oil was crystallized with ethanol and filtered to give 4-tert-butyl-2-{5-[2-(2-methylbenzenesulfonamidocarbonyl)phenylmethoxy]benzofuran-2-yl}thiazole (0.28 g).

Aufarbeitung

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. washeluted with a mixture of chloroform and methanol (40:1)
  5. additionThe fractions containing object compound
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. customThe oil was crystallized with ethanol
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-762b4c9a6105470392fe773f99964897
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296495

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