Triethylamine → HCID 18936749, compound

HRID 357053Notes

Reaction equation

HRID 357053 reaction equation
Br[CH2:2][N:3]1[C:7](=[O:8])[CH2:6][S:5][C:4]1=[O:9].[SH:10][C:11]1[N:16]2[CH:17]=[CH:18][N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)C>[N:19]1[CH:18]=[CH:17][N:16]2[C:11]([S:10][CH2:2][N:3]3[C:7](=[O:8])[CH2:6][S:5][C:4]3=[O:9])=[CH:12][CH:13]=[CH:14][C:15]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18936862HCID 18936862, compoundHCID 178418687HCID 178418687, compound

Product 1

HCID 18936749HCID 18936749, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen atmosphere, 2.10 g (10 mmol) of 3-bromomethylthiazolidine-2,4-dione was added to a solution of 1.50 g (10 mmol) of 5-mercaptoimidazo[1,2-a]pyridine and 1.67 ml (10 mmol) of triethylamine in 50 ml of ethanol, followed by stirring at room temperature for 16 hours. After the solvent was distilled off, the residue was dissolved in dichloromethane, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, ethyl acetate) to yield 1.41 g (50.5%, light brown solid) of the desired product.

Workup

  1. distillationAfter the solvent was distilled off
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with saturated aqueous sodium hydrogen carbonate
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent, ethyl acetate)

Sources & evidence

ORD record
ord-04b215c98d5c42e8a7345d64ad38bbdf
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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