Water → HCID 44218770, compound

HRID 474189Notes

Reaction equation

HRID 474189 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][S:7][C:8]2[C:9](=[O:17])[N:10]([CH2:14][CH2:15][CH3:16])[CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[Na].[OH:21]OS([O-])=O.[K+].[OH2:27]>O1CCCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][S:7]([C:8]2[C:9](=[O:17])[N:10]([CH2:14][CH2:15][CH3:16])[CH:11]=[CH:12][N:13]=2)(=[O:21])=[O:27])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 5360545SodiumHCID 23707502Potassium hydroxy sulfiteHCID 44218926HCID 44218926, compound

Product 1

HCID 44218770HCID 44218770, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 360 mg (1.17 mM) of 3-[(4-chlorobenzyl)thio]-1-propylpyrazin-2(1H)-one and 107.7 mg (1.28 mM) of sodium hydrogenocarbonate in 2 ml of tetrahydrofurane were added 2.9 g (4.7 mM) of oxone in 2 ml of water. The reaction mixture was stirred for 3 h at room temperature. Water was added and the aqueous layer was extracted with ethyle acetate. The organic layer was separated and washed with water, dried on anhydrous sodium sulfate and evaporated under vacuum. The residue was taken up in diisopropyle oxide, filtered and washed with diisopropyle oxide, to give 90 mg of 3-[(4-chlorobenzyl)sulfonyl]-1-propylpyrazin-2(1H)-one. Yield: 23%.

Workup

  1. extractionthe aqueous layer was extracted with ethyle acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customevaporated under vacuum
  6. filtrationfiltered
  7. washwashed with diisopropyle oxide

Sources & evidence

ORD record
ord-4be4bf3f08044d06bcb687923cfc6b85
Source dataset
uspto-grants-2014_01
Patent number
US08637522B2

Reaction notes

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