Pyridine → N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide

HRID 730202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730202
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[CH:5][C:4]=1[S:16](Cl)(=[O:18])=[O:17].[C:20]1([NH2:27])[C:21]([NH2:26])=[CH:22][CH:23]=[CH:24][CH:25]=1.N1C=CC=CC=1>ClCCl>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:27][S:16]([C:4]1[CH:5]=[C:6]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])(=[O:18])=[O:17]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7243O-PhenylenediamineHCID 624992522-Methoxy-5-trifluoromethanesulfonyl-1-benzenesulfonyl chloride

Produkt 1

HCID 68948452N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-methoxy-5-trifluoromethanesulfonyl-1-benzenesulfonyl chloride (5 g) in dry dichloromethane (10 mL), benzene-1,2-diamine (5 g) was added followed by addition of dry pyridine (10 mL) at 0° C. The resulting deep red reaction mixture was then stirred at room temperature for 4 h. The reaction mixture was diluted with dichloromethane (250 mL). The contents were washed with saturated aqueous sodium chloride solution (50 mL) and saturated aqueous sodium carbonate solution (50 mL). The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc (7:1 to 4:1) to give N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide (6 g). LC: Tr 0.95 min, MS: 411 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 4.18 (bs, 2H), 4.21 (s, 3H), 6.43 (m, 2H), 6.57 (bs, 1H), 6.75 (dd, 1H), 7.02 (t, 1H), 7.35 (d, 1H), 8.22 (dd, 1H), 8.40 (d, 1H) ppm.

Aufarbeitung

  1. customThe resulting deep red reaction mixture
  2. washThe contents were washed with saturated aqueous sodium chloride solution (50 mL) and saturated aqueous sodium carbonate solution (50 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customwas purified by flash column chromatography
  7. washeluting with DCM/EtOAc (7:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5947a9a8f6b84f2aa59d49d6f26ef892
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582673B2

Notizen zur Reaktion

Wird geladen…