Tributyltin Chloride → HCID 23449202, compound

HRID 1839311Notes

Reaction equation

HRID 1839311 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[F:16][C:17]([F:29])([F:28])[C:18]([C:20]1[N:21]=[CH:22][N:23]2[CH:27]=[CH:26][S:25][C:24]=12)=[O:19].[CH2:30]([Sn:34](Cl)([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:29][C:17]([F:16])([F:28])[C:18]([C:20]1[N:21]=[CH:22][N:23]2[CH:27]=[C:26]([Sn:34]([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:30][CH2:31][CH2:32][CH3:33])[S:25][C:24]=12)=[O:19]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23449099HCID 23449099, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23449202HCID 23449202, compound

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 0.34 g of 7-trifluoroacetylimidazo[5,1-b]thiazole and 0.48 ml of tri-n-butylstannyl chloride in 16 ml of dry THF in an argon atmosphere at −40° C. 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, 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=4:1) to give 0.14 g of the title compound.

Workup

  1. washby washing with water and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f8b8e8f52dc148e1b2025295b4b608e3
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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