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Triethylamine → 7-(t-Butyldimethylsilylsulfamoyl)imidazo[5,1-b]thiazole

HRID 989848
Notes
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Reaction equation

HRID 989848 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:16]([C:20]1[N:21]=[CH:22][N:23]2[CH:27]=[CH:26][S:25][C:24]=12)(=[O:19])(=[O:18])[NH2:17].C(OCC)(=O)C>CN(C=O)C>[Si:1]([NH:17][S:16]([C:20]1[N:21]=[CH:22][N:23]2[CH:27]=[CH:26][S:25][C:24]=12)(=[O:19])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 234491397-Sulfamoylimidazo[5,1-b]thiazole

Product 1

HCID 178110667-(t-Butyldimethylsilylsulfamoyl)imidazo[5,1-b]thiazoleYield 108.8%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

t-Butyldimethylsilyl chloride (0.30 g) and 0.33 ml of triethylamine were added to a solution of 0.20 g of 7-sulfamoylimidazo[5,1-b]thiazole in 5ml of DMF. The mixture was stirred at room temperature for one hr. Ethyl acetate was added to the reaction mixture, followed by washing with water and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 0.34 g of 7-(t-butyldimethylsilylsulfamoyl)imidazo[5,1-b]thiazole.

Workup

  1. washby washing with water and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e9ccdbaa84dd4a24908599001879875e
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06458780B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes