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

HRID 5479Notes

Reaction equation

HRID 5479 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)ethylthioimidazo[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) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 2 hours. The reaction mixture was washed in turn with aqueous saturated sodium bicarbonate 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 mixture was washed in turn with aqueous saturated sodium bicarbonate and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-13653be87d9a426aafa7e7ae72c1fdf7
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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