Acetonitrile → 5-[3-(Benzenesulfonamido)propyloxy]imidazo[1,2-a]pyridine

HRID 5460

Reaction equation

HRID 5460 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.C(#N)C.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:27]1([S:33]([NH:3][CH2:4][CH2:5][CH2:6][O:7][C:8]2[N:13]3[CH:14]=[CH:15][N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 233629975-[3-(Amino)propyloxy]imidazo[1,2-a]pyridine dihydrochloride

Product 1

HCID 233629785-[3-(Benzenesulfonamido)propyloxy]imidazo[1,2-a]pyridineYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-[3-(amino)propyloxy]imidazo[1,2-a]pyridine dihydrochloride (2.64 g, 10 mmoles) and triethylamine (4.88 ml, 35 mmoles) in methylene chloride (100 ml)-acetonitrile (30 ml) was added benzenesulfonyl chloride (1.53 ml, 12 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the crude product thus obtained was recrystallized from methylene-ethanol to obtain 1.97 g of the desired product (59.5%, light brown crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. washThe reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe crude product thus obtained
  7. customwas recrystallized from methylene-ethanol

Sources & evidence

ORD record
ord-87ae7e60b3f94aeab00f82581b06295a
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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