1-Bromo-3-chloropropane → 5-[3-(Chloro)propylthio]imidazo[1,2-a]pyridine

HRID 5437Notes

Reaction equation

HRID 5437 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][Cl:15].C(N(CC)CC)C>C(O)C>[Cl:15][CH2:14][CH2:13][CH2:12][S:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 178418687HCID 178418687, compound

Product 1

HCID 233628815-[3-(Chloro)propylthio]imidazo[1,2-a]pyridineYield 72.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (5.02 g, 33.4 mmoles) and 1-bromo-3-chloropropane (5.26 g, 33.4 mmoles) in ethanol (100 ml) was added triethylamine (4.66 ml, 33.4 mmoles) and the mixture was stirred at room temperature for 17 hours. After the solvent was distilled off, chloroform was added to the residue, which was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 5.46 g of the desired product (72.0%, light brown oily product).

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. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-877f58037d2241b39b1ba3a388bcb737
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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