Benzoyl chloride → 5-[3-(Benzoyloxy)propylthio]imidazo[1,2-a]pyridine

HRID 1608617Notes

Reaction equation

HRID 1608617 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:22]([O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 233628905-[3-(Hydroxy)propylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233629675-[3-(Benzoyloxy)propylthio]imidazo[1,2-a]pyridineYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 moles) and triethylamine (0.80 ml, 5.74 moles) in methylene chloride (25 ml) was added benzoyl chloride (1.10 ml, 11.6 moles) with stirring at room temperature and the mixture was further stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous 1N sodium hydroxide solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent: hexane/acetone (1:1)] to obtain 1.32 g of the desired product (88.1%, white solid).

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 minutes
  2. washThe reaction mixture was washed with an aqueous 1N sodium hydroxide solution
  3. customdried
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography [eluent: hexane/acetone (1:1)]

Sources & evidence

ORD record
ord-0554ed3755dd4225ad4415933e430f29
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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