Water → 5-[2-(Methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 5438

Reaction equation

HRID 5438 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.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>C(Cl)Cl>[CH3:21][S:22]([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:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 152293635-[2-(Methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridineYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (9.63 g, 49.8 mmoles) and triethylamine (7.64 ml) in methylene chloride (150 ml) was added methanesulfonyl chloride (3.85 ml, 49.7 mmoles) with stirring under ice-cooling and was stirred under ice-cooling for 1 hour. The reaction solution was poured into water and stirred. Then, the crystals precipitated were filtered off, washed with water and dried to obtain 10.53 g of the desired product (77.9%, colorless crystals).

Workup

  1. temperaturecooling
  2. stirringwas stirred under ice-
  3. temperaturecooling for 1 hour
  4. stirringstirred
  5. customThen, the crystals precipitated
  6. filtrationwere filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-0a019c1a317748ecb8ef899b9168024f
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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