Imidazole → HCID 18360047, compound

HRID 382603Notes

Reaction equation

HRID 382603 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C>[Si:16]([O:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18359893HCID 18359893, compound

Product 1

HCID 18360047HCID 18360047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.42 mg of 7-hydroxymethylimidazo[5,1-b]thiazole in 15 ml of DMF were added under ice-cooling 1.4 g of imidazole and 2.73 g of t-butyldimethylsilylchloride, and the mixture was stirred at the same temperature for 2 hours. DMF was removed under reduced pressure, and the residue was extracted two times with ethyl acetate. The organic layer was washed two times with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and removed under reduced pressure to give 7-(t-butyldimethylsilyloxy)methylimidazo[5,1-b]thiazole in a yield of 4.02 g.

Workup

  1. customDMF was removed under reduced pressure
  2. extractionthe residue was extracted two times with ethyl acetate
  3. washThe organic layer was washed two times with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customremoved under reduced pressure

Sources & evidence

ORD record
ord-beb4c313943d4d9db8192736aedb19c2
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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