Triethylamine → 5-[6-(Phthalimido)hexylthio]imidazo[1,2-a]pyridine

HRID 5453Notes

Reaction equation

HRID 5453 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][CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].C(N(CC)CC)C>C(O)C>[C:19]1(=[O:28])[N:18]([CH2:17][CH2:16][CH2:15][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:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 141120N-(6-Bromohexyl)phthalimideHCID 178418687HCID 178418687, compound

Product 1

HCID 199569985-[6-(Phthalimido)hexylthio]imidazo[1,2-a]pyridineYield 75.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (1.50g, 10 mmoles) and N-[6-(bromo)hexyl]phthalimide (3.10 g, 10 mmoles) in ethanol (100 ml) was added triethylamine (2.1 ml, 15 mmoles) and the mixture was stirred at room temperature for 12 hours. 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 2.86 g of the desired product (75.5%, light tan solid).

Workup

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

Sources & evidence

ORD record
ord-27f5598901a84909a3b45c27115d5a04
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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