Tributyltin Chloride → 7-(4-Nitrobenzylsulfamoyl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 1839300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839300
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC.[N+:17]([C:20]1[CH:38]=[CH:37][C:23]([CH2:24][NH:25][S:26]([C:29]2[N:30]=[CH:31][N:32]3[CH:36]=[CH:35][S:34][C:33]=23)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([O-:19])=[O:18].[CH2:39]([Sn:43](Cl)([CH2:48][CH2:49][CH2:50][CH3:51])[CH2:44][CH2:45][CH2:46][CH3:47])[CH2:40][CH2:41][CH3:42].[Cl-].[NH4+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.C(OCC)(=O)C>[N+:17]([C:20]1[CH:38]=[CH:37][C:23]([CH2:24][NH:25][S:26]([C:29]2[N:30]=[CH:31][N:32]3[CH:36]=[C:35]([Sn:43]([CH2:44][CH2:45][CH2:46][CH3:47])([CH2:48][CH2:49][CH2:50][CH3:51])[CH2:39][CH2:40][CH2:41][CH3:42])[S:34][C:33]=23)(=[O:27])=[O:28])=[CH:22][CH:21]=1)([O-:19])=[O:18]

Komponenten

8

Edukt 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 234493057-(4-Nitrobenzylsulfamoyl)imidazo[5,1-b]thiazoleHCID 86588928Lithium bis(trimethylsilyl)amide hexane

Produkt 1

HCID 234491917-(4-Nitrobenzylsulfamoyl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

A 1.0 N lithiumbis(trimethylsilyl)amide/n-hexane solution (4.8 ml) was added to a solution of 0.68 g of 7-(4-nitrobenzylsulfamoyl)imidazo[5,1-b]thiazole in 20 ml of THF and 4 ml of HMPA in an argon atmosphere at −40° C. The mixture was stirred at the same temperature for 30 min. Tri-n-butylstannyl chloride (0.57 ml) was added thereto. The mixture was stirred at the same temperature for 30 min. A saturated aqueous ammonium chloride solution was added thereto. Ethyl acetate was then added thereto. The mixture was then washed with water and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 0.78 g of the tile compound.

Aufarbeitung

  1. stirringThe mixture was stirred at the same temperature for 30 min
  2. washThe mixture was then washed with water and saturated brine in that order
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-6102f56013fb47f48d01b96592fb7cd4
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677331B2

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