Dichloromethane → HCID 44219554, compound

HRID 512110Notes

Reaction equation

HRID 512110 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-f26e3e71e412452fb3a2321f2f825880
Source dataset
uspto-grants-2015_08
Patent number
US09102632B2

Reaction notes

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