O-Toluidine → 4-Bromo-N-(2-methylphenyl)benzenesulfonamide

HRID 1710390

Reaktionsgleichung

Reaktionsgleichung von HRID 1710390
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[C:16]1[CH:21]=CC(S(Cl)(=O)=O)=[CH:18][CH:17]=1.NC1C(C)=CC=CC=1>ClCCl.C([O-])([O-])=O.[K+].[K+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:14]2[CH:18]=[CH:17][CH:16]=[CH:21][C:13]=2[CH3:12])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 7242O-ToluidineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 72132421-((4-Bromophenyl)sulfonyl)azetidine2×

Produkt 1

HCID 5719104-Bromo-N-(2-methylphenyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

The title compound is analogously synthesized as described for 1-(4-bromo-benzenesulfonyl)-azetidine (compound C3) from 1.28 g of 4-bromo-benzenesulfonyl chloride, 643 mg of commercially available o-toluidine in 20 ml of dichloromethane and 10 ml of K2CO3 solution. Purification by chromatography on flash silica gel (eluent: neat dichloromethane) affords 830 mg of the title compound as colorless, amorphous solid of m.p. 114° C. GC-MS: 327.0 (MH+). TLC: Rf=0.58 (neat dichloromethane).

Aufarbeitung

  1. customPurification by chromatography on flash silica gel (eluent: neat dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-84f56517186545b68eed49afed10cdbc
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790710B2

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