Water → Ethanethioic acid,s-(2-imidazo[1,5-a]pyrazin-3-ylethyl)ester

HRID 566251Notes

Reaction equation

HRID 566251 reaction equation
Cl[CH2:2][CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]2=[CH:6][N:5]=1.[C:13]([O-:16])(=[S:15])[CH3:14].[K+].O>CN(C=O)C>[C:13]([S:15][CH2:2][CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]2=[CH:6][N:5]=1)(=[O:16])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 212658743-(2-Chloroethyl)imidazo[1,5-a]pyrazineHCID 23670855Potassium ethanethioate

Product 1

HCID 21265778Ethanethioic acid,s-(2-imidazo[1,5-a]pyrazin-3-ylethyl)esterYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-chloroethyl)imidazo[1,5-a]pyrazine (1.51 g) in DMF (10 ml) was added potassium thioacetate (1.23 g). The mixture was stirred for 4 hours at room temperature. To the reaction mixture was added water. The mixture was subjected to extraction with ethyl acetate (50 ml×4). The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to column chromatography (carrier: silica gel, 60 g, developing solvent: ethyl acetate) to give the title compound (1.65 g) as colorless solid product.

Workup

  1. extractionThe mixture was subjected to extraction with ethyl acetate (50 ml×4)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9b954b256eb149028d69ba171848cd16
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

Loading…