Triethylamine → 5-[2-[2-(Phthalimido)ethyloxy]ethylthio]imidazo[1,2-a]pyridine

HRID 5454Notes

Reaction equation

HRID 5454 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][O:14][CH2:15][CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27].C(N(CC)CC)C>C(O)C>[C:18]1(=[O:27])[N:17]([CH2:16][CH2:15][O: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:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130286112-(2-(2-bromoethoxy)ethyl)-2,3-dihydro-1H-isoindole-1,3-dioneHCID 178418687HCID 178418687, compound

Product 1

HCID 233629035-[2-[2-(Phthalimido)ethyloxy]ethylthio]imidazo[1,2-a]pyridineYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[2-[2-(bromo)ethyloxy]ethyl]phthalimide (5.96 g, 20 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 12 hours and heated at reflux for 3 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 4.00 g of the desired product (54.5%, light tan solid).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  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-dedb6ba551c5410abf6790b1b72cd0d0
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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