Acetic Acid → HCID 19605016, compound

HRID 1603489Notes

Reaction equation

HRID 1603489 reaction equation
[C:1]([OH:4])(=O)C.C(O)=O.[NH2:8][CH2:9][C:10]1[S:14][C:13]2=[CH:15][N:16]=[CH:17][N:12]2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>O.ClCCl>[CH:1]([NH:8][CH2:9][C:10]1[S:14][C:13]2=[CH:15][N:16]=[CH:17][N:12]2[CH:11]=1)=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 11430Potassium CarbonateHCID 19605081HCID 19605081, compound

Product 1

HCID 19605016HCID 19605016, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 0.14 ml of acetic acid and 0.28 ml of formic acid which had been beforehand reacted with each other at 50° C. for 15 minutes was added to 3 ml of dry dichloromethane containing 154.6 mg of 2-aminomethylimidazo[5,1-b]thiazole at room temperature, and the mixture was then stirred at room temperature for 1 hour. Then, 2 ml of water was added to the reaction solution, and the solution was alkalified with anhydrous potassium carbonate under stirring. The solution was extracted with dichloromethane (15 ml×3). The combined organic layer was dried over anhydrous magnesium sulfate and then filtered, and the solvent was then evaporated under reduced pressure. The resulting crude product was purified by a silica gel column chromatograph to obtain 118.4 mg of the title compound as a colorless solid.

Workup

  1. stirringunder stirring
  2. extractionThe solution was extracted with dichloromethane (15 ml×3)
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was then evaporated under reduced pressure
  6. customThe resulting crude product was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-1f0ebe8f81294ff08ae2dfe984198949
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

Loading…