1-Bromo-2-isothiocyanatobenzene → N-[4-Chloro-2-hydroxy-3-[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2-bromophenyl)thiourea

HRID 1840336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840336
[CH3:1][N:2]([CH3:15])[S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([NH2:13])[C:7]=1[OH:14])(=[O:5])=[O:4].[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]=[C:24]=[S:25]>CN(C)C=O>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]([NH:13][C:24]([NH:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Br:16])=[S:25])=[C:7]([OH:14])[C:6]=1[S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4]

Komponenten

4

Edukt 2

HCID 6116541-Bromo-2-isothiocyanatobenzeneHCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

Produkt 1

HCID 10183328N-[4-Chloro-2-hydroxy-3-[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2-bromophenyl)thioureaAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N,N-dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (50 mg, 0.2 mmol) and 2-bromophenylisothiocyanate (43 mg, 0.2 mmol) in 0.5 mL of N,N-dimethylformamide was stirred at room temperature for 3 hours. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v) to give the desired product (66 mg, 74%). EI-MS (m/z) 465.5 (M+).

Aufarbeitung

  1. customPurification by column chromatography on silica gel
  2. washeluting with ethyl acetate/hexane (30/70

Quellen und Nachweise

ORD-Eintrag
ord-158688e7cbe740acb3c71e64a1cc6189
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680317B2

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