Tributyltin Chloride → HCID 23449091, compound

HRID 1839303Notes

Reaction equation

HRID 1839303 reaction equation
[C:1]([NH:4][CH2:5][C:6]([C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[CH:14][S:13][C:12]=12)=[O:7])(=[O:3])[CH3:2].[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[Cl-].[NH4+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[C:1]([NH:4][CH2:5][C:6]([C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[C:14]([Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])[S:13][C:12]=12)=[O:7])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23449031HCID 23449031, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23449091HCID 23449091, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

7-Acetylaminoacetylimidazo[5,1-b]thiazole (397 mg) was dissolved in 40 ml of THF and 8 ml of HMPA. Tri-n-butylstannyl chloride (0.76 ml) and 7.1 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added dropwise in that order in an argon atmosphere at −73° C. The mixture was stirred at the same temperature for one hr. An ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed twice with brine, 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 (eluting with ethyl acetate and then with dichloromethane:methanol=20:1) to give 152 mg of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed twice with brine
  3. dry with materialdried 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 (
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-bb158e78f8364cca82204ffde20a2bb5
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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