3-Chlorobenzenesulphonyl chloride → 4-[4-Chloro-3-(3-chloro-benzenesulfonylamino)-benzoylamino]-benzoic acid ethyl ester

HRID 2241145

Reaktionsgleichung

Reaktionsgleichung von HRID 2241145
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-])=O)[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].[Cl:25][C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([NH:20][S:32]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[CH:27]=3)(=[O:34])=[O:33])[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2]

Komponenten

3

Edukt 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 711250Ethyl 4-[(4-chloro-3-nitrobenzoyl)amino]benzoate

Produkt 1

HCID 675497574-[4-Chloro-3-(3-chloro-benzenesulfonylamino)-benzoylamino]-benzoic acid ethyl ester

Versuchsvorschrift

4-[4-Chloro-3-(3-chloro-benzenesulfonylamino)-benzoylamino]-benzoic acid, MS (ISP): m/e=463.1 (M+H+), was prepared in analogy to example 1, steps A to D. Step A was performed using 4-chloro-3-nitro-benzoyl chloride and yielded 4-(4-chloro-3-nitro-benzoylamino)-benzoic acid ethyl ester. This was reduced to 4-(4-Chloro-3-nitro-benzoylamino)-benzoic acid ethyl ester in step B. This was coupled with 3-chloro-benzenesulfonyl chloride in step C, yielding 4-[4-chloro-3-(3-chloro-benzenesulfonylamino)-benzoylamino]-benzoic acid ethyl ester, which was hydrolyzed in step D.

Quellen und Nachweise

ORD-Eintrag
ord-ba9ea59c8bdb44959eee2006ec0655c8
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723538B2

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