Tributyltin Chloride → HCID 23447644, compound

HRID 1840430Notes

Reaction equation

HRID 1840430 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[N:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][S:39][C:40]1[N:41]=[CH:42][N:43]2[CH:47]=[CH:46][S:45][C:44]=12)=[N+:31]=[N-:32].[Cl-].[NH4+]>C1COCC1>[N:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][S:39][C:40]1[N:41]=[CH:42][N:43]2[CH:47]=[C:46]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH2:3][CH3:4])[S:45][C:44]=12)=[N+:31]=[N-:32]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23447648HCID 23447648, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23447644HCID 23447644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butylstannyl chloride (0.969 ml) and 5.66 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added to a solution of 636 mg of 7-(6-azidohexyl)thioimidazo[5,1-b]thiazole in 20 ml of THF at −40° C. under an argon atmosphere. The mixture was stirred for 45 min. An aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to prepare 1.01 g of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washby washing with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation
  5. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)
  6. customto prepare 1.01 g of the title compound

Sources & evidence

ORD record
ord-95c53f5572b941bfba6bb56293a30a43
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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