Benzyl Isothiocyanate → 1-Benzyl-3-(7-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]naphthalen-1-yl)thiourea

HRID 412358

Reaktionsgleichung

Reaktionsgleichung von HRID 412358
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([O:12][C:13]1[CH:14]=[CH:15][C:16]3[N:20]=[C:19]([CH2:21][O:22][C:23]4[CH:36]=[CH:35][C:26]([CH2:27][CH:28]5[S:32][C:31](=[O:33])[NH:30][C:29]5=[O:34])=[CH:25][CH:24]=4)[N:18]([CH3:37])[C:17]=3[CH:38]=1)[CH:8]=[CH:7]2.[CH2:39]([N:46]=[C:47]=[S:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1>[CH2:39]([NH:46][C:47]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]3[CH:14]=[CH:15][C:16]4[N:20]=[C:19]([CH2:21][O:22][C:23]5[CH:24]=[CH:25][C:26]([CH2:27][CH:28]6[S:32][C:31](=[O:33])[NH:30][C:29]6=[O:34])=[CH:35][CH:36]=5)[N:18]([CH3:37])[C:17]=4[CH:38]=3)[CH:10]=2)[CH:5]=[CH:4][CH:3]=1)=[S:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Komponenten

4

Edukt 2

HCID 2346Benzyl IsothiocyanateHCID 98327115-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione

Produkt 1

HCID 103052621-Benzyl-3-(7-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]naphthalen-1-yl)thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.4 g) in anhydrous tetrahydrofuran (10 ml) was added benzyl isothiocyanate (0.24 g) and the mixture was stirred at room temperature for 5.5 hours and then at 50° C. for 9 hours. The reaction mixture was concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:1→3:1 as the eluant to afford the title compound (0.36 g, Rf=0.53: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=3:1).

Aufarbeitung

  1. waitat 50° C. for 9 hours
  2. concentrationThe reaction mixture was concentrated
  3. customThe residue was chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-f2920676c5d5441f87a7bf7e8e1c8e95
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

Verknüpfte Notizen

Wird geladen…