Citric Acid → HCID 10125594, compound

HRID 2217983Notes

Reaction equation

HRID 2217983 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[C:16](Cl)=[N:15][CH:14]=[CH:13][N:12]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.C(O)(=O)[CH2:19][C:20]([CH2:25][C:26](O)=O)([C:22]([OH:24])=[O:23])[OH:21]>C[O-].[Na+].CO>[C:22]([O:24][CH2:16][CH3:11])(=[O:23])[CH3:20].[CH3:2][CH2:26][CH2:25][CH:20]([CH3:19])[CH3:22].[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[C:16]([O:21][CH3:20])=[N:15][CH:14]=[CH:13][N:12]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 311Citric AcidHCID 10215019HCID 10215019, compound

Product 2

HCID 10125594HCID 10125594, compoundHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

5-Chloro-N-(3-chloro-2-pyrazinyl)-2-thiophenesulphonamide (Example 25a) (0.03 g) in sodium methoxide in methanol (1.5 mL of a 10% solution) was heated at 85° C. After 4 h, 5% aqueous citric acid (10.0 mL) was added and the mixture extracted with ethyl acetate (2×30 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 (0.026 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×30 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-d40d61eb24174bd9bdff27d70d819381
Source dataset
uspto-grants-2008_08
Patent number
US07410972B2

Reaction notes

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