p-Bromobenzenesulfonyl chloride → 4-Bromo-N-[4-chloro-2-(pyridine-4-carbonyl)-phenyl]-benzenesulfonamide

HRID 29529

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[C:20]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)=[O:21]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[C:20]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-Bromo-benzenesulfonyl chloride 27.5 g (107 mmol) was dissolved in 180 ml of anhydrous pyridine. To this solution was added (2-amino-5-chloro-phenyl)-pyridin-4-yl-methanone 25 g (107 mmol). The reaction mixture was stirred under nitrogen 5 hour at 80° C. and pyridine was then evaporated under vacuum. The resulting crude material was dissolved in dichloromethane, and extracted with saturated bicarbonate solution. The combined organic layer was washed with brine dried over magnesium sulfate, filtered and concentrated, then ethyl acetate (50 mL) added to the solid, the solid was filtered, washed again with ethyl acetate, to yield a pale yellow solid: LC-MSD, m/z for C18H12BrClN2O3S [M+H]+: 452.9

Workup

custompyridine was then evaporated under vacuum
dissolutionThe resulting crude material was dissolved in dichloromethane
extractionextracted with saturated bicarbonate solution
washThe combined organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
additionethyl acetate (50 mL) added to the solid
filtrationthe solid was filtered
washwashed again with ethyl acetate
customto yield a pale yellow solid

Sources & evidence

ORD record: ord-83614b2a73924137bac68b7eedc2daea
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420055B2

Linked notes

Loading…