Water → 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide

HRID 2224390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2224390
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[N+:7]([C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].C(N(CC)CC)C.O>O1CCOCC1>[N+:7]([C:10]1[CH:11]=[C:12]([S:16]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 9773Ethanamine, 2,2,2-trifluoro-

Produkt 1

HCID 692881143-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,2,2-trifluoroethylamine (1.17 ml, 15 mmol) in dioxane (37 ml) was added at room temperature 3-nitrobenzenesulfonyl chloride (3.0 g, 14 mmol) and triethylamine (2.06 ml, 15 mmol). The light yellow suspension was stirred at room temperature for 4 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) to yield 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide (3.18 g, 83%) as a light yellow solid. MS (ISP) 283.9 [(M−H)−].

Aufarbeitung

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-fababdeaa52c4851a3df810a4461d813
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378417B2

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