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

HRID 989835Notes

Reaction equation

HRID 989835 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-86b7465cf28a4d16b4d2f376e8710c63
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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