Citric Acid → 2,3-Dichloro-N-[3-(2-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

HRID 1443962Notes

Reaction equation

[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19]([NH:22][C:23]1[C:28](Cl)=[N:27][CH:26]=[CH:25][N:24]=1)(=[O:21])=[O:20].[C:30](O)(=O)[CH2:31][C:32](CC(O)=O)(C(O)=O)[OH:33]>COCCOC>[C:32]([O:10][CH2:9][CH3:4])(=[O:33])[CH3:31].[CH3:14][CH2:15][CH2:16][CH:17]([CH3:12])[CH3:30].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19]([NH:22][C:23]1[C:28]([O:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)=[N:27][CH:26]=[CH:25][N:24]=1)(=[O:20])=[O:21]

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydride (0.05 g of a 60% dispersion in oil) was added to pyridine-2-methanol (0.088 g) in 1,2-dimethoxyethane (3.0 mL). After 5 minutes, 2,3-dichloro-N-(3-chloro-2-pyrazinyl)benzenesulphonamide (0.1 g) was added and the mixture heated at 70° C. After 4 h, 5% aqueous citric acid (10 mL) was added and the mixture extracted with ethyl acetate (2×50 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 (0.06 g).

Workup

waitAfter 4 h
extractionthe mixture extracted with ethyl acetate (2×50 mL)
washThe combined extracts were washed with brine
dry with materialdried (MgSO4)
customthe solvent evaporated

Sources & evidence

ORD record: ord-96aa17351bb04f72a91123a7b13d570c
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662825B2

Reaction notes

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