Diethylamine → 2-Chloro-N,N-diethylnicotinamide

HRID 1043452

Reaktionsgleichung

Reaktionsgleichung von HRID 1043452
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12]>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:13]([CH2:14][CH3:15])[CH2:11][CH3:12])=[O:5]

Komponenten

4

Edukt 2

HCID 8021DiethylamineHCID 27745412-Chloronicotinoyl chloride

Produkt 1

HCID 44659442-Chloro-N,N-diethylnicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a 1-neck round-bottom flask under an atmosphere of nitrogen was dissolved 2-chloronicotinoyl chloride (2.12 g, 0.0120 mol) in methylene chloride (25 mL) and the reaction cooled to 0° C. N-ethylethanamine (2.7 mL, 0.026 mol) was added to the mixture and stirred at 0° C. for 2 hours and then at 20° C. for 16 hours. The reaction was extracted with dichloromethane and the organic extracts were washed with water, brine, dried (MgSO4), and concentrated in vacuo. The crude product was used in the next reaction without further purification. 1H NMR (400 MHz, CDCl3): δ 8.42-8.44 (m, 1H), 7.64-7.65 (m, 1H), 7.29-7.63 (m, 1H), 3.75-3.79 (m, 1H), 3.35-3.40 (m, 1H), 3.13-3.22 (m, 2H), 1.82 (t, 3H), 1.088 (t, 3H). MS: [M+1]=213.

Aufarbeitung

  1. waitat 20° C. for 16 hours
  2. extractionThe reaction was extracted with dichloromethane
  3. washthe organic extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was used in the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b500e312c17f4925bc8d5a4fc44445d9
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563541B2

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