Triethylamine → 5-[2-(Methylcarbamoyloxy)ethylthio]imidazo[1,2-a]pyridine

HRID 1608601Notes

Reaction equation

HRID 1608601 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.C(N(CC)CC)C.[CH3:21][N:22]=[C:23]=[O:24]>C(Cl)Cl>[CH3:21][NH:22][C:23]([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:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 144568495-[2-(Hydroxy)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628175-[2-(Methylcarbamoyloxy)ethylthio]imidazo[1,2-a]pyridineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(hydroxy)ethylthio]imidazo[1,2-a]pyridine (971 mg, 5 mmoles) and trietylamine (0.91 ml, 6.53 mmoles) in methylene chloride (40 ml) was added methyl isocyanate (0.65 ml, 11 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 12 hours. The reaction mixture was washed with saturtated saline and dried over anhydrous magnesium sulfater. After the solvent was distilled off, the residue was purified by column chromatography (eluent: methanol/chloroform=1:20) to obtain 1.07 g of the desired product (85.2%, colorless crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. washThe reaction mixture was washed with saturtated saline
  4. dry with materialdried over anhydrous magnesium sulfater
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: methanol/chloroform=1:20)

Sources & evidence

ORD record
ord-a5aefb578de64f57b6086b41813d6bf4
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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