2,6-Lutidine → 2,6-Lutidine hydrochloride

HRID 1370599

Reaktionsgleichung

Reaktionsgleichung von HRID 1370599
[N:1]1[C:6]([CH3:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].C1(S([Cl:23])(=O)=O)C(F)=C(F)C(F)=C(F)C=1F.S(Cl)(Cl)(=O)=O>CC(C)=O.NC1C=CC=CC=1>[ClH:23].[N:1]1[C:6]([CH3:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8]

Komponenten

6

Edukt 3

HCID 79372,6-LutidineHCID 24648Sulfuryl chlorideHCID 700262,3,4,5,6-Pentafluorobenzenesulfonyl chloride

Produkt 1

HCID 5191162,6-Lutidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6115AnilineLösungsmittel2×

Versuchsvorschrift

Aniline 9.3 (44.6 g, 268 mmol) and 2,6-lutidine (32.8 mL, 282 mmol) were dissolved in 800 mL of acetone (the aniline only partly dissolved). An addition funnel was charged with C6F5SO2Cl (41.8 mL, 282 mmol) and the sulfonyl chloride was added over 15 minutes. During the addition, the starting material dissolved and a new precipitate (2,6-lutidine hydrochloride) formed. After 30 minutes, the 2,6-lutidine hydrochloride was removed by filtration and the filtrate concentrated under reduced pressure. The brown oily solid so produced was triturated with CH2Cl2 and the solid collected. A second batch of product was obtained by repeating the concentration, trituration, and filtration. After drying under high vacuum, 95.5 g (90%) of sulfonamide 9.4 was obtained as a pale yellow solid.

Aufarbeitung

  1. dissolutiononly partly dissolved)
  2. additionDuring the addition
  3. dissolutionthe starting material dissolved

Quellen und Nachweise

ORD-Eintrag
ord-dde246ed10664faf9b7ae3be31c59a55
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583165B2

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