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

HRID 5432Notes

Reaction equation

HRID 5432 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][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([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])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 144568495-[2-(Hydroxy)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233629605-[2-(Methylsulfonyloxy)ethylthio]imidazo[1,2-a]pyridineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(hydroxy)ethylthio]imidazo[1,2-a]pyridine (9.71 g, 50 mmoles) and triethylamine (10.5 ml, 75.3 mmoles) in methylene chloride (300 ml) was added methanesulfonyl chloride (4.26 ml, 55 mmoles) with stirring under ice-cooling and the mixture was stirred under ice-cooling for 2 hours. The reaction solution was washed in turn with an aqueous saturated sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off to obtain 13.6 g of the desired product (quantitative, brown oily product).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 2 hours
  4. washThe reaction solution was washed in turn with an aqueous saturated sodium bicarbonate solution and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-c14424b657b147a5b1cf7290b793d4e0
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

Loading…