1,2-Dichloro-3-isocyanatobenzene → N-[4-chloro-2-hydroxy-3-(N''-methylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl) urea

HRID 2301506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301506
[CH3:1][NH:2][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].[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[N:23]=[C:24]=[O:25]>CN(C)C=O.C(OCC)(=O)C>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]([NH:13][C:24]([NH:23][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=2[Cl:15])=[O:25])=[C:7]([OH:14])[C:6]=1[S:3]([NH:2][CH3:1])(=[O:5])=[O:4]

Komponenten

5

Edukt 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 18373530N-Methyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

Produkt 1

HCID 10137198N-[4-chloro-2-hydroxy-3-(N''-methylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl) ureaAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-methyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (70 mg, 0.29 mmol) and 2,3-dichlorophenylisocyanate (57 μL, 0.44 mmol) in 2 mL of N,N-dimethylformamide was stirred at room temperature for 66 hours. The mixture was diluted with ethyl acetate and washed with water to give the crude material. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v), gave the desired product (60 mg, 49%, three steps). EI-MS (m/z) 422.3, 424.3, 426.3 (M−).

Aufarbeitung

  1. washwashed with water
  2. customto give the crude material
  3. customPurification by column chromatography on silica gel
  4. washeluting with ethyl acetate/hexane (30/70

Quellen und Nachweise

ORD-Eintrag
ord-d7d628bc042f47309995c95d4d8e016f
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06500863B1

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