Citric Acid → N-(4-Chlorophenyl)-3-methoxy-benzenesulfonamide

HRID 2079603

Reaktionsgleichung

Reaktionsgleichung von HRID 2079603
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1.N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=2)(=[O:19])=[O:18])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 1049PyridineHCID 78124-ChloroanilineHCID 27375043-Methoxybenzenesulfonyl chloride

Produkt 1

HCID 57788151N-(4-Chlorophenyl)-3-methoxy-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 4-chloroaniline (400 mg, 3.13 mmol) in anhydrous dichloromethane (40 mL) were added 3-methoxybenzenesulfonyl chloride (648 mg, 3.13 mmol) followed by pyridine (297.2 mg, 3.76 mmol). The mixture was allowed to stir for 12 h at 25° C. 10% citric acid solution (20 mL) and water (20 mL) was added. The organic phase was dried (Na2SO4), and evaporated under reduced pressure yielding the title compound as solid which was used as such in the next step. Yield: 900 mg (96%). MS (m/e): 296 (M+−H); 1H-NMR (CDCl3, 400 MHz): δ 3.76 (s, 3H), 6.48 (brs, 1H), 7.0 (d, J=8.72 Hz, 2H), 7.06 (d, J=7.76 Hz, 1H), 7.21 (m, 3H), 7.32 (m, 2H).

Aufarbeitung

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bf36f5f2bdfa42f99f69fd1332a065ac
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932269B2

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