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

HRID 5440
Notes
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Reaction equation

HRID 5440 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.[CH2:21]([S:23](Cl)(=[O:25])=[O:24])[CH3:22]>C(Cl)Cl>[CH2:21]([S:23]([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:25])=[O:24])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 152293645-[2-(Ethylsulfonylamino)ethylthio]imidazo[1,2-a]pyridineYield 78.2%

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) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (100 ml) was added ethanesulfonyl chloride (0.95 ml, 10 mmoles) at room temperature with stirring and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed in turn with an aqueous saturated sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:5) to obtain 2.23 g of the desired product (78.2%, colorless crystals).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. washThe reaction mixture was washed in turn with an aqueous saturated sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:5)

Sources & evidence

ORD record
ord-b37486258c7548529fd7103f125f8261
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244908

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes