1,2-Dichloro-3-isocyanatobenzene → SB-332235

HRID 2301494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301494
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([Cl:8])=[CH:6][CH:7]=1.[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[N:22]=[C:23]=[O:24]>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:23]([NH:22][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=2[Cl:14])=[O:24])=[C:3]([OH:13])[C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10]

Komponenten

5

Edukt 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Produkt 1

HCID 9887803SB-332235Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (0.88 g, 3.9 mmol) and 2,3-dichlorophenylisocyanate (0.62 mL, 4.6 mmol) in 5 mL of N,N-dimethyl-formamide was stirred at room temperature for 20 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 to 50/50, v/v), followed by recrystallization from dichloromethane and hexane, gave the desired product (1.18 g, 74%). mp 241-242° C.

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 to 50/50
  5. customv/v), followed by recrystallization from dichloromethane and hexane

Quellen und Nachweise

ORD-Eintrag
ord-49f33536bdc04dc798e298d7b84f560c
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06500863B1

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