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

HRID 989835ノート

反応式

HRID 989835 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 12679Hexamethylphosphoramide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-86b7465cf28a4d16b4d2f376e8710c63
出典データセット
uspto-grants-2002_10
特許番号
US06458780B1

反応ノート

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