Citric Acid → HCID 10215905, compound

HRID 2217981Notes

Reaction equation

HRID 2217981 reaction equation
Cl[C:2]1[C:7](Cl)=[N:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[S:14][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[C:25](O)(=O)[CH2:26][C:27]([CH2:32][C:33]([OH:35])=O)([C:29]([OH:31])=[O:30])O.[CH3:38][N:39](C)C=O>>[C:29]([O:31][CH2:7][CH3:2])(=[O:30])[CH3:27].[CH3:10][CH2:33][CH2:32][CH:27]([CH3:26])[CH3:29].[Cl:9][C:10]1[S:14][C:13]([S:15]([NH:18][C:2]2[C:7]([O:35][CH2:33][C:32]3[CH:27]=[CH:26][CH:25]=[CH:38][N:39]=3)=[N:6][CH:5]=[CH:4][N:3]=2)(=[O:17])=[O:16])=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 12413015-Chlorothiophene-2-Sulfonamide

Product 2

HCID 10215905HCID 10215905, compoundHCID 21882781Isohexane ethyl acetate

Procedure

2,3-Dichloropyrazine (0.8 g), 5-chloro-2-thienylsulphonamide (1.1 g) and potassium carbonate (2.5 g) in N,N-dimethylformamide (20 mL) was heated at 75° C. After 16 h, 5% aqueous citric acid (10.0 mL) was added and the mixture extracted with ethyl acetate (2×20 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 (0.5 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×20 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-6c79248fd13540308c7a97e81bb3c842
Source dataset
uspto-grants-2008_08
Patent number
US07410972B2

Reaction notes

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