2-Dimethylaminopyridine → chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

HRID 432965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432965
[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].CN(C1C=CC=CN=1)C>ClCCl.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

6

Edukt 3

HCID 218852-DimethylaminopyridineHCID 677684-Fluoro-3-nitroanilineHCID 77054(Chloromethyl)sulfonyl chloride

Produkt 1

HCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamideAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

20 g of 4-fluoro-3-nitroaniline (128 mmol) was dissolved in a mixture of 200 mL of dichloromethane and 40 mL of pyridine. To this solution was added 21 g (140 mmol) of chloromethylsulfonyl chloride dropwise at 20-30° C., followed by the addition of 3.21 g of dimethylaminopyridine. The solution was stirred for an additional 3 hours. The reaction mixture was transferred into a separatory funnel and washed sequentially with water (twice with 25 mL), 5% HCl (twice with 25 mL), and water (25 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated under reduced pressure to yield 32 g (93%) of the title compound as a solid melting at 112-113° C.

Aufarbeitung

  1. customThe reaction mixture was transferred into a separatory funnel
  2. washwashed sequentially with water (twice with 25 mL), 5% HCl (twice with 25 mL), and water (25 mL)
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b166d96010af46608c77036a997a1fea
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664400B2

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