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Water → N-(2,4-Dimethoxybenzyl)-1-(3-bromophenyl)ethanesulfonamide

HRID 339867
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 339867
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:24][Li].CI.O>C1COCC1.C(OCC)C.C(OCC)(=O)C>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][S:9]([CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH3:24])(=[O:10])=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 68292274C-(3-Bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamideHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 68359259N-(2,4-Dimethoxybenzyl)-1-(3-bromophenyl)ethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Under inert gas, 3.50 g of C-(3-bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide were initially charged in 40 ml of THF, and then, at a temperature of −76° C., 10.93 ml of a 1.6 N methyllithium solution in diethyl ether were added dropwise and the mixture was stirred for 5 minutes. After the addition of 1.24 g of methyl iodide, the reaction mixture was allowed to come to room temperature. The reaction solution was admixed with water and ethyl acetate, and the aqueous phase was reextracted with ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation, and the residue was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (2.83 g) with a molecular weight of 414.3 g/mol (C17H20BrNO4S).

Aufarbeitung

  1. customto come to room temperature
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated by rotary evaporation
  4. customthe residue was purified by means of normal phase chromatography
  5. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-936de80ba6cb473eb19b935e6cda9d41
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08895547B2

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