Hydrochloric Acid → [5-(Methanesulfonyl)pyridin-2-yl]methanaminium chloride

HRID 1517474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517474
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)(=[O:4])=[O:3].C(O)C.[ClH:16]>[Pd].O>[ClH:16].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH2:12])=[N:9][CH:10]=1)(=[O:4])=[O:3]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 591699295-(Methylsulfonyl)pyridine-2-carbonitrile

Produkt 1

HCID 66725223[5-(Methanesulfonyl)pyridin-2-yl]methanaminium chlorideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 5-methanesulfonyl-pyridine-2-carbonitrile (3.0 kg, 1 mol eq, limiting reagent) was charged absolute ethanol (30.7 L, 10 rel vol), 32% aqueous 6 M hydrochloride acid (3.9 kg, 2 mol eq) and palladium on carbon (303 g, 1.50 g, 10% w/w). The reaction was stirred under a hydrogen atmosphere (2.5 bar) at 25° C. until the reaction was complete as judged by HPLC analysis. Water (5.4 L, 1.8 rel vol) was charged. The mixture was filtered through Celite and washed with water (1.8 L, 0.6 rel vol). The reaction mixture was concentrated under reduced pressure and ethanol (30.0 L, 10 rel vol) charged. The mixture was cooled, stirred and the product collected by filtration. The solid was washed with ethanol (16.9 L, 5.6 rel vol) and the solid dried to constant weight yielding the title compound (3.1 kg, 13.8 mol, 84%); 1H NMR (d6-DMSO): 9.10 (d, 1H, J=2.4 Hz), 8.73 (br s, 3H), 8.41 (dd, 1H, J 2.4, 8.3 Hz), 7.82 (d, 1H, J=8.2 Hz), 4.30-4.34 (m, 2H), 3.35 (s, 3H) ppm; LCMS: m/z 187.3 (MH+).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with water (1.8 L, 0.6 rel vol)
  3. concentrationThe reaction mixture was concentrated under reduced pressure and ethanol (30.0 L, 10 rel vol)
  4. additioncharged
  5. temperatureThe mixture was cooled
  6. stirringstirred
  7. filtrationthe product collected by filtration
  8. washThe solid was washed with ethanol (16.9 L, 5.6 rel vol)
  9. customthe solid dried to constant weight

Quellen und Nachweise

ORD-Eintrag
ord-bf6e4b4d17d44bbcae94027d50081885
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232296B2

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