Reaktion #66418

ord-59d62dffbe6b4068aed3341ed1d03a2c

Reaktionsgleichung

Cl
HCl
[Na+].[OH-]
NaOH
NS(=O)(=O)c1ccc(Cl)s1
5-chlorothiophenesulfonamide
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride
→
O=C(NS(=O)(=O)c1ccc(Cl)s1)c1ccc([N+](=O)[O-])cc1
titled compound
Ausbeute 81.0%
O=C(NS(=O)(=O)c1ccc(Cl)s1)c1ccc([N+](=O)[O-])cc1
N-[(5-chloro(2-thienyl))sulfonyl](4-nitrophenyl)carboxamide
Ausbeute 81.0%

Edukte

Cl
HCl
[Na+].[OH-]
NaOH
NS(=O)(=O)c1ccc(Cl)s1
5-chlorothiophenesulfonamide
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe precipitate was collected by filtration
  2. 2
    Sonstigedried
  3. 3
    SonstigeRecrystallization from EtOAc/hexane

Vorschrift

A 85 mg portion (0.43 mmol) of 5-chlorothiophenesulfonamide dissolved in 2 mL of acetone was treated with 110 μL of 4N NaOH (0.43 mmol) followed by addition of 80 mg (0.43 mmol) of 4-nitrobenzoyl chloride. After stirring for 12 h, the solution was acidfied 1N HCl and the precipitate was collected by filtration and dried. Recrystallization from EtOAc/hexane afforded 120 mg (81%) of the titled compound. ES-MS (M+H)+=347 (Cl).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524721B2uspto-grants-2013_09