Tributyltin Chloride → HCID 22631811, compound

HRID 1839325Notes

Reaction equation

HRID 1839325 reaction equation
C([Li])CCC.CCCCCC.[C:12]1([S:18][C:19]2[N:20]=[CH:21][N:22]3[CH:26]=[CH:25][S:24][C:23]=23)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:27]([Sn:31](Cl)([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[Cl-].[NH4+]>C1COCC1>[C:12]1([S:18][C:19]2[N:20]=[CH:21][N:22]3[CH:26]=[C:25]([Sn:31]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:27][CH2:28][CH2:29][CH3:30])[S:24][C:23]=23)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 22631972HCID 22631972, compoundHCID 23714775LiHMDS tetrahydrofuranHCID 178418244HCID 178418244, compound

Product 1

HCID 22631811HCID 22631811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

A 1.59 N n-butyl lithium/n-hexane solution (0.189 ml) was added dropwise at −73° C. in an argon atmosphere to a solution of 66.5 mg of 7-phenylthioimidazo[5,1-b]thiazole in 3 ml of THF. Subsequently, 0.098 ml of tri-n-butylstannyl chloride was added to the mixture. The mixture was stirred at the same temperature for 15 min. The temperature of the system was raised to −40° C. A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (0.11 ml) was added thereto. The mixture was stirred for one hr. An aqueous ammonium chloride solution was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give 115 mg of the title compound.

Workup

  1. stirringThe mixture was stirred for one hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0ade892c4fdf408fb0c612cd0b06ba06
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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