4-Methoxyphenol → N-[4-(4-Methoxy-phenoxy)-phenyl]-methanesulfonamide

HRID 1716300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716300
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl.CN(C)CC(O)=O>O1CCOCC1.CCOC(C)=O.[Cu]I>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1

Komponenten

8

Edukt 4

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 836147N-(4-iodophenyl)methanesulfonamide

Produkt 1

HCID 68517759N-[4-(4-Methoxy-phenoxy)-phenyl]-methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of N-(4-iodo-phenyl)-methanesulfonamide (0.45 g, 1.52 mmol) from Step A, 4-methoxyphenol (0.28 g, 2.28 mmol), Cs2CO3 (0.99 g, 3.04 mmol), N,N-dimethylglycine HCl salt (31.8 mg, 0.23 mmol) and CuI (14.5 mg, 0.076 mmol) in dioxane (4 mL) under N2 was heated to 100 C overnight. The reaction was diluted with EtOAc and brought to the usual work-up. The residue was purified by chromatography (silica gel, 30% EtOAc/hexanes) to give the desired product. MS (EI) 294 (M+H)+.

Aufarbeitung

  1. temperaturewas heated to 100 C overnight
  2. customThe residue was purified by chromatography (silica gel, 30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a9c8034169a948b183255b3372e04166
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803793B2

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