Tributyltin Chloride → HCID 22631745, compound

HRID 1840428Notes

Reaction equation

HRID 1840428 reaction equation
C([Li])CCC.CCCCCC.[CH:12]([NH:14][CH2:15][CH2:16][S:17][C:18]1[N:19]=[CH:20][N:21]2[CH:25]=[CH:24][S:23][C:22]=12)=[O:13].[CH2:26]([Sn:30](Cl)([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29].[Cl-].[NH4+]>C1COCC1>[CH:12]([NH:14][CH2:15][CH2:16][S:17][C:18]1[N:19]=[CH:20][N:21]2[CH:25]=[C:24]([Sn:30]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:26][CH2:27][CH2:28][CH3:29])[S:23][C:22]=12)=[O:13]

Participants

6

Reactant 4

HCID 15096Tributyltin Chloride2×HCID 25517Ammonium ChlorideHCID 22632105HCID 22632105, compoundHCID 178418244HCID 178418244, compound2×

Product 1

HCID 22631745HCID 22631745, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.6 N n-butyllithium/n-hexane solution (11.7 ml) was added to a solution of 1.19 g of 7-(2-formylaminoethyl)thioimidazo[5,1-b]thiazole in 50 ml of THF at −55° C. under an argon atmosphere. The mixture was stirred at that temperature for 10 min. Tri-n-butylstannyl chloride (2.24 ml) was added thereto, and the mixture was stirred for 20 min. The temperature of the reaction solution was raised to −30° C. over a period of one hr, during which time 3.34 ml of a 1.6 N n-butyllithium/n-hexane solution and 2.4 ml of tri-n-butylstannyl chloride were added. 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 removed by distillation, and the residue was purified by column chromatography on silica gel (ethyl acetate only to dichloromethane:methanol=20:1) to prepare 1.615 g of the title compound.

Workup

  1. stirringthe mixture was stirred for 20 min
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washby washing with brine
  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 (ethyl acetate only to dichloromethane
  8. custommethanol=20:1) to prepare 1.615 g of the title compound

Sources & evidence

ORD record
ord-2c0babe6b75946848d5e52af4a494783
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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