Methyl chloroformate → 5-[2-(Methoxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 1608603

Reaction equation

HRID 1608603 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[C:22]([O:24][CH3:25])=[O:23]>C(Cl)Cl>[CH3:25][O:24][C:22]([NH:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1)=[O:23]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 98164115-[2-(Methoxycarbonylamino)ethylthio]imidazo[1,2-a]pyridineYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (30 ml ) was added methyl chloroformate (0.77 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10) to obtain 1.68 g of the desired product (66.9%, colorless crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 20 minutes
  3. washThe reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)

Sources & evidence

ORD record
ord-e219de9aefbd40beae7131ee4a096006
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Linked notes

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