Citric Acid → HCID 10308720, compound

HRID 1443964Notes

Reaction equation

HRID 1443964 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18](Cl)=[N:17][CH:16]=[CH:15][N:14]=1)(=[O:11])=[O:10].[C:20](O)(=O)C[C:22](CC(O)=O)([C:24]([OH:26])=[O:25])[OH:23]>C[O-].[Na+].CO>[C:24]([O:26][CH2:18][CH3:13])(=[O:25])[CH3:22].[CH3:4][CH2:5][CH2:6][CH:7]([CH3:2])[CH3:20].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([O:23][CH3:22])=[N:17][CH:16]=[CH:15][N:14]=1)(=[O:11])=[O:10]

Participants

6

Reactant 2

HCID 311Citric AcidHCID 591681672,3-Dichloro-N-(3-chloro-2-pyrazinyl)benzenesulphonamide

Product 2

HCID 10308720HCID 10308720, compoundHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

2,3-Dichloro-N-(3-chloro-2-pyrazinyl)benzenesulphonamide (Example 28 part a) (0.2 g) in 10% sodium methoxide in methanol (10 mL) was heated at 85° C. After 4 h, 5% aqueous citric acid (50 mL) was added and the mixture extracted with ethyl acetate (2×150 mL). The combined extracts were washed with brine, dried (MgSO4) and the solvent evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound as a white solid (0.12 g)

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×150 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-4380681f7ba84fa3b0e94fc87ec45e57
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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