Triethylamine → 5-[4-(Phthalimido)butylthio]imidazo[1,2-a]pyridine

HRID 1608607Notes

Reaction equation

HRID 1608607 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][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(N(CC)CC)C>C(O)C>[C:17]1(=[O:26])[N: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:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 93575N-(4-Bromobutyl)phthalimideHCID 178418687HCID 178418687, compound

Product 1

HCID 233628715-[4-(Phthalimido)butylthio]imidazo[1,2-a]pyridineYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00 g, 20 mmoles) and N-[4-(bromo)butyl]phthalimide (6.21 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 45 minutes. After the solvent was distilled off, chloroform was added to the residue, which was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent was distilled off. Then, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 4.50 g of the desired product (64.1%, pale yellow crystals).

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 minutes
  3. distillationAfter the solvent was distilled off
  4. additionchloroform was added to the residue, which
  5. washwas washed with saturated saline
  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-8e29b43bd74f4a4ab931aaa7a6d8ba19
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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