Dichloromethane → HCID 44219554, compound

HRID 474190Notes

Reaction equation

HRID 474190 reaction equation
[Br:1][C:2]1[N:3]=[C:4](SCC2C=CC(Cl)=CC=2)[C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=1.Cl[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27](OO)=O)[CH:22]=1.[S:31](S([O-])=O)([O-:34])(=O)=[O:32].[Na+].[Na+].[Cl:40]CCl>>[Br:1][C:2]1[N:3]=[C:4]([S:31]([CH2:27][C:23]2[CH:22]=[CH:21][C:26]([Cl:40])=[CH:25][CH:24]=2)(=[O:34])=[O:32])[C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 44219243HCID 44219243, compound

Product 1

HCID 44219554HCID 44219554, compoundYield 87%

Procedure

4.6 g (12.7 mM) of 5-bromo-3-[(4-chlorobenzyl)thio]-1-ethylpyrazin-2(1H)-one and 9.9 g (40 mM) of metachloroperbenzoic acid (70%) in 75 ml of dichloromethane were stirred for 10 min at room temperature. Aqueous 2M solution of sodium metabisulphite was added, the organic layer was separated and washed with an aqueous solution of hydrogenocarbonate, then with water and evaporated under vacuum. The residue was taken up in diisopropyle oxide. A solid was filtered and washed with diisopropyle oxide, to give 4.3 g of 5-bromo-3-[(4-chlorobenzyl)sulfonyl]-1-ethylpyrazin-2(1H)-one. Yield: 87%.

Workup

  1. customthe organic layer was separated
  2. washwashed with an aqueous solution of hydrogenocarbonate
  3. customwith water and evaporated under vacuum
  4. filtrationA solid was filtered
  5. washwashed with diisopropyle oxide

Sources & evidence

ORD record
ord-a1f2d1d645b84f9db4a451d2d449496b
Source dataset
uspto-grants-2014_01
Patent number
US08637522B2

Reaction notes

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