Citric Acid → 5-Chloro-N-[6-chloro-3-(2-furanylmethoxy)-2-pyrazinyl]-2-thiophenesulphonamide

HRID 2217976Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

Sodium hydride (0.04 g of a 60% dispersion in oil) was added to furfurylalcohol (0.034 g) in 1,2-dimethoxyethane (1.0 mL). After 5 minutes 5-chloro-N-(3-bromo-6-chloro-2-pyrazinyl)-2-thiophenesulphonamide (0.1 g) was added and the mixture heated at 40° C. After 16 h, 5% aqueous citric acid (5.0 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 dichloromethane gave the title compound as a white solid (0.03 g).

Workup

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

Sources & evidence

ORD record: ord-3157029e9720439c9cc7377e4fb98984
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410972B2

Reaction notes

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