Triethylamine → 5-chloro-N,N-dimethylpyrazine-2-carboxamide

HRID 1027697

Reaktionsgleichung

Reaktionsgleichung von HRID 1027697
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([N:13]([CH3:14])[CH3:12])=[O:9])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 152157435-Chloropyrazine-2-carbonyl chloride

Produkt 1

HCID 590004705-chloro-N,N-dimethylpyrazine-2-carboxamideAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

5-chloropyrazine-2-carbonyl chloride (2.13 gram, 12.05 mmol) and dimethylamine HCl salt (1.06 gram, 12.7 mmol) were suspended in dichloromethane (50 mL) with stirring. Triethylamine (5.04 mL, 36.2 mmol) in dichloromethane (25 mL) was added dropwise at 0° C. to the reaction mixture. The combined solution was warmed up to ambient temperature and stirred for 4 hours. The compound was diluted with dichloromethane, washed with 1N HCl, water, brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography (silica gel, gradient of 30 to 80% ethyl acetate in heptane) to provide desired 5-chloro-N,N-dimethylpyrazine-2-carboxamide (SM-1: 2.24 g, 85%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.74 (d, J=1.37 Hz, 1H) 8.53 (d, J=1.37 Hz, 1H) 3.15 (s, 3H) 3.12 (s, 3H)

Aufarbeitung

  1. stirringstirred for 4 hours
  2. washwashed with 1N HCl, water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, gradient of 30 to 80% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-5aa1f562001546f6b62359321c919f0f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735396B2

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