Methyl Isocyanate → 5-[2-(Methylcarbamoylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 5445

Reaction equation

HRID 5445 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.[CH3:14][N:15]=[C:16]=[O:17]>C(Cl)Cl>[CH3:14][NH:15][C:16]([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:17]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 539413315-[2-(Methylcarbamoylamino)ethylthio]imidazo[1,2-a]pyridineYield 86%

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) in methylene chloride (30 ml) was added methyl isocyanate (0.59 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:5) to obtain 2.15 g of the desired product (86.0%, pale yellow crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 1 hour
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:5)

Sources & evidence

ORD record
ord-852f02fa664542a2bdf8f02b66d9841f
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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