Tributyltin Chloride → HCID 23449080, compound

HRID 1839323Notes

Reaction equation

HRID 1839323 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.[CH3:30][NH:31][S:32]([N:35]([CH2:41][C:42]([C:44]1[N:45]=[CH:46][N:47]2[CH:51]=[CH:50][S:49][C:48]=12)=[O:43])[S:36]([NH:39][CH3:40])(=[O:38])=[O:37])(=[O:34])=[O:33].[Cl-].[NH4+]>C1COCC1>[CH3:30][NH:31][S:32]([N:35]([CH2:41][C:42]([C:44]1[N:45]=[CH:46][N:47]2[CH:51]=[C:50]([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:49][C:48]=12)=[O:43])[S:36]([NH:39][CH3:40])(=[O:37])=[O:38])(=[O:33])=[O:34]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23714775LiHMDS tetrahydrofuranHCID 86758539HCID 86758539, compound

Product 1

HCID 23449080HCID 23449080, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butylstannyl chloride (0.962 ml) and 8.42 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were sequentially added at −73° C. in an argon atmosphere to a solution of 485 mg of 7-(N,N-dimethylaminosulfonylamino)acetyl-imidazo[5,1-b]thiazole in 18 ml of THF. The mixture was stirred at the same temperature for 30 min. 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=1:1) to give 427 mg of the title compound.

Workup

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

Sources & evidence

ORD record
ord-a870e0aaeb4c47308bb16775729a2082
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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