Tributyltin Chloride → HCID 22631437, compound

HRID 1840425Notes

Reaction equation

HRID 1840425 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][S:35][C:36]1[N:37]=[CH:38][N:39]2[CH:43]=[CH:42][S:41][C:40]=12)=[N+:31]=[N-:32].[Cl-].[NH4+]>C1COCC1>[N:30]([CH2:33][CH2:34][S:35][C:36]1[N:37]=[CH:38][N:39]2[CH:43]=[C:42]([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:41][C:40]=12)=[N+:31]=[N-:32]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 22631545HCID 22631545, compoundHCID 23714775LiHMDS tetrahydrofuran2×

Product 1

HCID 22631437HCID 22631437, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butylstannyl chloride (3.53 ml) and 12.34 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added to a solution of 2.32 g of 7-(2-azidoethyl)thioimidazo[5,1-b]thiazole in 75 ml of THF at −65° C. under an argon atmosphere. The temperature of the mixture was raised to −30° C. over a period of 2 hr, during which time a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (1.0 ml) was added to the mixture four times. An aqueous ammonium chloride solution was added to the reaction mixture, 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 4.62 g of the title compound.

Workup

  1. additionwas added to the mixture four times
  2. extractionthe mixture was extracted with ethyl acetate
  3. washby washing with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation
  6. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)
  7. customto prepare 4.62 g of the title compound

Sources & evidence

ORD record
ord-982005f6b7084d97b60d5b9bb3e62db0
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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