Tributyltin Chloride → 7-(N-Methoxy-N-methylsulfamoyl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 989845Notes

Reaction equation

HRID 989845 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[CH3:16][O:17][N:18]([CH3:30])[S:19]([C:22]1[N:23]=[CH:24][N:25]2[CH:29]=[CH:28][S:27][C:26]=12)(=[O:21])=[O:20].[CH2:31]([Sn:35](Cl)([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH3:34].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH3:16][O:17][N:18]([CH3:30])[S:19]([C:22]1[N:23]=[CH:24][N:25]2[CH:29]=[C:28]([Sn:35]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:31][CH2:32][CH2:33][CH3:34])[S:27][C:26]=12)(=[O:20])=[O:21]

Participants

7

Reactant 4

HCID 15096Tributyltin Chloride2×HCID 25517Ammonium ChlorideHCID 23449100HCID 23449100, compoundHCID 23714775LiHMDS tetrahydrofuran2×

Product 1

HCID 234492297-(N-Methoxy-N-methylsulfamoyl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (2.0 ml) was added to a solution of 0.44 g of 7-(N-methoxy-N-methylsulfamoyl)imidazo[5,1-b]thiazole in 9 ml of dry THF in an argon atmosphere at −40° C. The mixture was stirred at the same temperature for 30 min. Tri-n-butylstannyl chloride (0.58 ml) was added thereto. The mixture was stirred for 30 min. Further, a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (2.5 ml) was then added, followed by stirring for 30 min. Tri-n-butylstannyl chloride (0.1 ml) was added thereto. The mixture was stirred at the same temperature for 30 min. A saturated aqueous ammonium chloride solution was added thereto, and the ethyl acetate was then added, followed by washing 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=1:2) to give 0.39 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-2e40d5e314a8442ba7b7ec5dc95ce7d0
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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