Pyridine → 5-[2-(Phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridine

HRID 1608587Notes

Reaction equation

HRID 1608587 reaction equation
[OH: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.N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>C(Cl)Cl>[O:23]([C:21]([O: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:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 144568495-[2-(Hydroxy)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628305-[2-(Phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridineYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(hydroxy)ethylthio]imidazo[1,2-a]pyridine (5.83 g, 30 mmoles) and pyridine (4.36 ml, 60 mmoles) in methylene chloride (120 ml) was added phenyl chloroformate (7.53 ml, 60 mmoles) with stirring under ice-cooling and the mixture was stirred under ice-cooling for 30 minutes. The reaction solution was washed in turn with an aqueous 5% sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 8.61 g of the desired product (91.3%, oily product).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 30 minutes
  4. washThe reaction solution was washed in turn with an aqueous 5% sodium bicarbonate solution and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-cc4040d9d2354989a05cc0169040b164
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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