Triethylamine → Ethanamine,2-(imidazo[1,2-a]pyridin-5-ylthio)-n-methyl-

HRID 5480

Reaction equation

HRID 5480 reaction equation
CS(O[CH2:6][CH2:7][S:8][C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1)(=O)=O.[CH2:18]([N:20](CC)CC)C.CN.CO>C(Cl)(Cl)Cl>[CH3:18][NH:20][CH2:6][CH2:7][S:8][C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 233629605-[2-(Methylsulfonyloxy)ethylthio]imidazo[1,2-a]pyridineHCID 57454252Monomethylamine methanol

Product 1

HCID 23362988Ethanamine,2-(imidazo[1,2-a]pyridin-5-ylthio)-n-methyl-Yield 47.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-[2-(methylsulfonyloxy)etylthio]imidazo[1,2-a]pyridine (2.18 g, 8 mmoles), triethylamine (2.24 ml, 16 mmoles) and a 40% methylamine-methanol solution (20 ml) in chloroform (20 ml) was heated at reflux for 3 hours. The reaction mixture was washed with 3N NaOH and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography [eluent: methanol/chloroform (1:10)] to obtain 781 mg of the desired product (47.1%, light brown oily product).

Workup

  1. temperatureat reflux for 3 hours
  2. washThe reaction mixture was washed with 3N NaOH
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography [eluent: methanol/chloroform (1:10)]

Sources & evidence

ORD record
ord-7c20f62d01794f2e832a1780e09e3e32
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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