Citric Acid → HCID 10194762, compound

HRID 2217972Notes

Reaction equation

HRID 2217972 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[Cl:8][C:9]1[S:13][C:12]([S:14]([NH:17][C:18]2[C:23](Br)=[N:22][C:21]([Br:25])=[CH:20][N:19]=2)(=[O:16])=[O:15])=[CH:11][CH:10]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>COCCOC.C(OCC)(=O)C>[Cl:8][C:9]1[S:13][C:12]([S:14]([NH:17][C:18]2[C:23]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:22][C:21]([Br:25])=[CH:20][N:19]=2)(=[O:16])=[O:15])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 10288068HCID 10288068, compound

Product 1

HCID 10194762HCID 10194762, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methoxyethanol (0.04 g) was added to a stirred suspension of sodium hydride (0.05 g of 60%) in 1,2-dimethoxyethane (5 mL). After 10 minutes, 5-chloro-N-(3,5-dibromo-2-pyrazinyl)-2-thiophenesulphonamide (0.2 g) was added. After 30 minutes, 5% aqueous citric acid and ethyl acetate were added. The organic layer was separated dried (MgSO4) and the solvent was evaporated. Chromatography on silica eluting with hexane/ethyl acetate gave the title compound.

Workup

  1. waitAfter 30 minutes
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bdc1216064a640d18dacb294f6a08c4b
Source dataset
uspto-grants-2008_08
Patent number
US07410972B2

Reaction notes

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