Pyridine → 4-chloro-N-(2-methoxyphenyl)-3-nitrobenzenesulfonamide

HRID 346781

Reaktionsgleichung

Reaktionsgleichung von HRID 346781
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][O:16][C:17]1[C:18](N)=[CH:19][CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:16][CH3:15])(=[O:9])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 70002-MethoxyanilineHCID 73244-Chloro-3-nitrobenzenesulfonamide

Produkt 1

HCID 28876834-chloro-N-(2-methoxyphenyl)-3-nitrobenzenesulfonamideAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Chloro-3-nitrobenzenesulfonamide (1.73 g, 6.78 mmol) was dissolved in CH2Cl2 (7.0 mL). o-Anisidine (1.00 g, 8.13 mmol) was added dropwise at room temperature, followed by a slow addition of pyridine (2.0 mL). After 16 h of continued stirring, the reaction mixture was diluted with EtOAc (50 mL) and washed with 1 M HCl (3×50 mL). The organic phase was dried (MgSO4) filtered and evaporated to a brown solid, upon which re-crystallization from ethanol/water gave 2.22 g (95%) of the product as white crystals. 1H NMR (CDCl3) δ 8.20 (s, 1H), 7.80 (dd, 1H), 7.56 (d, 1H), 7.53 (d, 1H), 7.13 (t, 1H), 6.96 (t, 1H), 6.76 (d, 1H), 3.66 (s, 3H). The sulfonamide proton was not observed.

Aufarbeitung

  1. washwashed with 1 M HCl (3×50 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to a brown solid, upon which re-crystallization from ethanol/water

Quellen und Nachweise

ORD-Eintrag
ord-8484466154f6489cac225193b4362624
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173035B2

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