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

HRID 1839300노트

반응식

HRID 1839300 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 12679Hexamethylphosphoramide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6102f56013fb47f48d01b96592fb7cd4
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677331B2

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