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

HRID 1081722Notes

Reaction equation

HRID 1081722 reaction equation
[SH:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C(N(CC)CC)C>C(O)C>[C:16]1(=[O:25])[N:15]([CH2:14][CH2:13][CH2:12][S:1][C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21611N-3-BromopropylphthalimideHCID 178418687HCID 178418687, compound

Product 1

HCID 233629415-[3-(Phthalimido)propylthio]imidazo[1,2-a]pyridineYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00 g, 20 mmoles) and N-[3-(bromo)propyl]phthalimide (5.90 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 1 hour and heated at reflux for 1 hour. After the solvent was distilled off, chloroform was added to the residue, which was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off. Then, the residue was purified by column chromatography (eluent:ethyl acetate) to obtain 4.79 g of the desired product (71.1%, colorless crystals).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. distillationAfter the solvent was distilled off
  4. additionchloroform was added to the residue, which
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThen, the residue was purified by column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-566c385a011a4d188b5d3a19881006c7
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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