Triethylamine → 5-(Phthalimidomethylthio)imidazo[1,2-a]pyridine

HRID 1608604Notes

Reaction equation

HRID 1608604 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][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C(N(CC)CC)C>C(O)C>[C:14]1(=[O:23])[N: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:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 178418687HCID 178418687, compound

Product 1

HCID 233628645-(Phthalimidomethylthio)imidazo[1,2-a]pyridineYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00 g, 20 mmoles) and N-bromomethylphthalimide (5.28 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. 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 4.29 g of the desired product (69.4%, pale yellow crystals).

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-aa89be8d96504f4cb91fb287211e894a
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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