Water → HCID 14323477, compound

HRID 568573Notes

Reaction equation

HRID 568573 reaction equation
[O-]CC.[Na+].[CH2:5]([SH:7])[CH3:6].Cl[C:9]1[C:10]([C:15](=[O:18])[CH2:16][CH3:17])=[N:11][CH:12]=[CH:13][N:14]=1.O>C(O)C>[CH2:5]([S:7][C:9]1[C:10]([C:15](=[O:18])[CH2:16][CH3:17])=[N:11][CH:12]=[CH:13][N:14]=1)[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 2723922Sodium ethoxideHCID 14323475HCID 14323475, compound

Product 1

HCID 14323477HCID 14323477, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of sodium ethoxide (100 mg, 1.47 mmoles) and ethanethiol (110 mg, 1.77 mmoles) in 7 ml of absolute ethanol is stirred under nitrogen at room temperature for 10 minutes. 1-(3-Chloro-2-pyrazinyl)-1-propanone (250 mg, 1.47 mmoles) in 5 ml absolute ethanol is added to the above mixture, and the reaction mixture is stirred for 4 hours at which time thin layer chromatography indicates that all of the starting materials have reacted. The mixture is poured into water (100 ml) and extracted with methylene chloride (3×10 ml), and the extracts are combined and washed with water (1×50 ml) and saturated NaCl solution (1×50 ml). After drying (MgSO4), the solvent is removed under reduced pressure to give an 87% yield of 1-(3-ethylthio-2-pyrazinyl)-1-propanone (m.p. 45°-48° C.).

Workup

  1. stirringthe reaction mixture is stirred for 4 hours at which time thin layer chromatography
  2. customhave reacted
  3. extractionextracted with methylene chloride (3×10 ml)
  4. washwashed with water (1×50 ml) and saturated NaCl solution (1×50 ml)
  5. dry with materialAfter drying (MgSO4)
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-0d792d2dac6d40c1bc3df2ce5ae1e0fb
Source dataset
uspto-grants-1988_03
Patent number
US04728738

Reaction notes

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