Triethylamine → 5-[3-[2-(Phenyl)ethylcarbonyloxy]propylthio]imidazo[1,2-a]pyridine

HRID 1081734Notes

Reaction equation

HRID 1081734 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]1([CH2:28][CH2:29][C:30](Cl)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1([CH2:28][CH2:29][C:30]([O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]2[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 233628905-[3-(Hydroxy)propylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233629325-[3-[2-(Phenyl)ethylcarbonyloxy]propylthio]imidazo[1,2-a]pyridineYield 84.2%

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 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added 3-phenylpropionyl chloride (1.01 g, 5.99 mmoles) with stirring at room temperature and the mixture was further stirred at room temperature for 2 hours. 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 1.37 g of the desired product (84.2%, yellow oily product).

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hours
  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-eb12ec41072e4857b27a3346b81ec2fe
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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