Hydrochloric Acid → chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

HRID 1289358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1289358
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][CH2:13][S:14](Cl)(=[O:16])=[O:15].Cl>N1C=CC=CC=1>[Cl:12][CH2:13][S:14]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)(=[O:16])=[O:15]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 677684-Fluoro-3-nitroanilineHCID 77054(Chloromethyl)sulfonyl chloride

Produkt 1

HCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 4-fluoro-3-nitroaniline (23.4 g, 0.15 mol) in anhydrous pyridine (120 mL) was added dropwise a solution of chloromethylsulfonyl chloride (22.35 g, 0.15 mol) at 0° C. under a nitrogen atmosphere. The mixture was then stirred at 0°-5° C. for 4 h and then the mixture was poured onto ice (1500 g) containing concentrated aqueous hydrochloric acid (300 mL). The mixture was filtered, and the residue was dissolved in methylene chloride (1200 mL). After drying (MgSO4) and concentration under reduced pressure, the crude product was dissolved in 1-chlorobutane:ether 9:1 v/v and passed through silica gel. The eluent was concentrated under reduced pressure to give the title compound of Step A.

Aufarbeitung

  1. additionthe mixture was poured onto ice (1500 g)
  2. filtrationThe mixture was filtered
  3. dissolutionthe residue was dissolved in methylene chloride (1200 mL)
  4. customAfter drying
  5. concentration(MgSO4) and concentration under reduced pressure
  6. dissolutionthe crude product was dissolved in 1-chlorobutane:ether 9:1 v/v
  7. concentrationThe eluent was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7051ce36ee3f4f6e984b6d82efdfc800
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750471

Notizen zur Reaktion

Wird geladen…