Sodium hydride → [(4-Chlorophenyl)-(3-methoxy-benzenesulphonyl)-amino]-acetic acid methyl ester

HRID 2079604

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>C1COCC1>[CH3:27][O:26][C:24](=[O:25])[CH2:23][N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)(=[O:11])=[O:10]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of N-(4-chlorophenyl)-3-methoxy-benzenesulfonamide (900 mg, 3.02 mmol) in anhydrous THF (40 mL) was added sodium hydride (146 mg, 3.62 mmol) at 0-5° C. under nitrogen. The mixture was stirred at 25° C. for 30 minutes. Methyl bromoacetate (463 mg, 3.02 mmol) was then added, stirred for 1 h at 25° C. A further amount of methyl bromoacetate (232 mg, 1.51 mmol) was added, and stirring continued for another 12 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate (3×20 ml). The combined organic layer was washed with water, dried (Na2SO4), evaporated under reduced pressure to yield the title compound as oily compound, which was used as such in the next step. Yield: 1.03 g (92%).

Aufarbeitung

stirringstirred for 1 h at 25° C
stirringstirring
waitcontinued for another 12 h
customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
extractionextracted with ethyl acetate (3×20 ml)
washThe combined organic layer was washed with water
dry with materialdried (Na2SO4)
customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-97bbd1237ad14f33a5318303ad7f683c
Quelldatensatz: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07932269B2

Verknüpfte Notizen

Wird geladen…