Water → 5-[2-(Acetylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 1081714Notes

Reaction equation

HRID 1081714 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24].O>CN(C)C=O>[C:23]([NH:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 233628335-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine dihydrochloride

Product 1

HCID 233628825-[2-(Acetylamino)ethylthio]imidazo[1,2-a]pyridineYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine dihydrochloride (2.66 g, 10 mmoles) and triethylamine (4.32 ml, 31 mmoles) in N,N-dimethylformamide (24 ml) was added acetyl chloride (0.71 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:3) to obtain 1.57 g of the desired product (66.8%, colorless crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:3)

Sources & evidence

ORD record
ord-0561531abd1b4cafb91701953164856e
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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