Oxalyl chloride → N-[(5-chloro(2-thienyl))sulfonyl]-N'-[4-(5-chloro-1,3-dioxobenzo [c]azolidin-2-yl)-3-methylphenyl]ethane-1,2-diamide

HRID 38139

Reaktionsgleichung

Reaktionsgleichung von HRID 38139
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22](=[O:23])[C:21]3[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:20]=3[C:19]2=[O:29])=[C:14]([CH3:30])[CH:13]=1.[C:31](Cl)(=[O:35])[C:32](Cl)=[O:33]>>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:31](=[O:35])[C:32]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[C:22](=[O:23])[C:21]4[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:20]=4[C:19]3=[O:29])=[C:14]([CH3:30])[CH:13]=2)=[O:33])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 65578Oxalyl chlorideHCID 93991N-(4-Amino-o-tolyl)-4-chlorophthalimideHCID 12413015-Chlorothiophene-2-Sulfonamide

Produkt 1

HCID 20800257N-[(5-chloro(2-thienyl))sulfonyl]-N'-[4-(5-chloro-1,3-dioxobenzo [c]azolidin-2-yl)-3-methylphenyl]ethane-1,2-diamideAusbeute 44 %

Versuchsvorschrift

A 200 mg (1.0 mmol) of 5-chlorothiophenesulfonamide was slurried in 0.5 mL of oxalyl chloride and refluxed for 6 h. The solvent was removed in vacuo and 36 mg of the resulting solid was dissolved in 240 μL acetonitrile and treated with 40 mg (0.14 mmol) 2-(4-amino-2-methylphenyl)-5-chlorobenzo[c]azoline-1,3-dione. After stirring for 1 h, the solvent was removed and the residue was purified by RP-HPLC to give 33 mg (44%) of the titled compound. ES-MS (M+H)+=538(2Cl).

Aufarbeitung

  1. temperaturerefluxed for 6 h
  2. customThe solvent was removed in vacuo and 36 mg of the resulting solid
  3. dissolutionwas dissolved in 240 μL acetonitrile
  4. customthe solvent was removed
  5. customthe residue was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9ec4754677b44b32a431031ad2edb79d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524721B2

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