Tributyltin Chloride → HCID 23449330, compound

HRID 1839292Notes

Reaction equation

HRID 1839292 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][NH:13][S:14]([C:17]1[N:18]=[CH:19][N:20]2[CH:24]=[CH:23][S:22][C:21]=12)(=[O:16])=[O:15].[CH2:25]([Sn:29](Cl)([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28].[Cl-].[NH4+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.C(OCC)(=O)C>[CH3:12][NH:13][S:14]([C:17]1[N:18]=[CH:19][N:20]2[CH:24]=[C:23]([Sn:29]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:25][CH2:26][CH2:27][CH3:28])[S:22][C:21]=12)(=[O:15])=[O:16]

Participants

8

Reactant 4

HCID 15096Tributyltin Chloride2×HCID 25517Ammonium ChlorideHCID 23449178HCID 23449178, compoundHCID 178418244HCID 178418244, compound2×

Product 1

HCID 23449330HCID 23449330, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A 1.6 N n-butyllithium/n-hexane solution (1.6 ml) was added to a solution of 0.26 g of 7-(N-methylsulfamoyl)imidazo[5,1-b]thiazole in 8 ml of dry THF and 4 ml of HMPA in an argon atmosphere at −50° C. The mixture was stirred at the same temperature, for 30 min. Tri-n-butylstannyl chloride (0.34 ml) was added thereto. The mixture was stirred four 30 min. A 1.6 N n-butyllithium/n-hexane solution (0.8 ml) was further added thereto. The mixture was stirred for 30 min. Tri-n-butylstannyl chloride (0.2 ml) was added thereto, followed by stirring at the same temperature for 30 min. A saturated aqueous ammonium chloride solution was added thereto. 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=12) to give 0.39 g of the title compound.

Workup

  1. stirringThe mixture was stirred four 30 min
  2. stirringThe mixture was stirred for 30 min
  3. stirringby stirring 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=12)

Sources & evidence

ORD record
ord-5ae187659bd34f6190bf43199ae2a0d5
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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