Acetic Acid → HCID 19605080, compound

HRID 1603477Notes

Reaction equation

HRID 1603477 reaction equation
[C:1]([OH:4])(=O)C.C(O)=O.[CH3:8][NH:9][CH2:10][C:11]1[N:12]2[CH:18]=[N:17][CH:16]=[C:13]2[S:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O.ClCCl>[CH:1]([N:9]([CH2:10][C:11]1[N:12]2[CH:18]=[N:17][CH:16]=[C:13]2[S:14][CH:15]=1)[CH3:8])=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 11430Potassium CarbonateHCID 19605154HCID 19605154, compound

Product 1

HCID 19605080HCID 19605080, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 0.25 ml of anhydrous acetic acid and 0.50 ml of formic acid which had been beforehand reacted with each other at 50° C. for 5 minutes was added to 6 ml of a dichloromethane solution containing 294 mg of 3-(N-methylamino)methylimidazo[5,1-b]thiazole under ice-cooling, followed by stirring at the same temperature for 30 minutes. Then, water was added to the reaction solution, and the solution was then alkalified with anhydrous potassium carbonate under stirring, followed by extraction three times with dichloromethane. The organic layer was dried over anhydrous potassium carbonate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 174 mg of the title compound.

Workup

  1. temperaturecooling
  2. stirringunder stirring
  3. extractionfollowed by extraction three times with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-5726a5d42a3247e394ae30e9c40d79ac
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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