Ammonium Chloride → HCID 19605074, compound

HRID 1603497Notes

Reaction equation

HRID 1603497 reaction equation
C[Mg]Br.[CH2:4](OCC)C.[CH:9]([C:11]1[N:12]2[CH:18]=[N:17][CH:16]=[C:13]2[S:14][CH:15]=1)=[O:10].[Cl-].[NH4+]>C1COCC1>[OH:10][CH:9]([C:11]1[N:12]2[CH:18]=[N:17][CH:16]=[C:13]2[S:14][CH:15]=1)[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15379550HCID 15379550, compoundHCID 178467822HCID 178467822, compound

Product 1

HCID 19605074HCID 19605074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 1 ml of a 3.0M methylmagnesium bromide-diethyl ether solution was added dropwise to 15 ml of an anhydrous THF solution containing 304 mg of 3- formylimidazo[5,1-b]thiazole at -78° C., and the mixture was then stirred at the same temperature for 3.5 hours. Further, an aqueous ammonium chloride solution was added to the reaction solution, and the solution was then extracted three times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 296 mg of the title compound as a colorless crystal.

Workup

  1. extractionthe solution was then extracted three times with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-b2e05456e74d48ad80dbdf718494b7c9
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

Loading…