Triethylamine → N-(5-Methylpyridin-2-yl)pivalamide

HRID 1008826

Reaktionsgleichung

Reaktionsgleichung von HRID 1008826
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.CCN(CC)CC.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>C(Cl)Cl>[CH3:16][C:17]([CH3:22])([CH3:21])[C:18]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)=[O:19]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 153482-Amino-5-methylpyridineHCID 62493Pivaloyl chloride

Produkt 1

HCID 4182924N-(5-Methylpyridin-2-yl)pivalamideAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-methylpyridin-2-amine (200 g, 1.85 mol) in anhydrous CH2Cl2 (1000 mL) was added dropwise a solution of Et3N (513 mL, 3.70 mol) and 2,2-dimethyl-propionyl chloride (274 mL, 2.22 mol) at 0° C. under N2. The ice bath was removed and stirring was continued at room temperature for 2 hours. The reaction was poured into ice (2000 g). The organic layer was separated and the remaining aqueous layer was extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4 and evaporated to afford 2,2-dimethyl-N-(5-methyl-pyridin-2-yl)-propionamide (350 g), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=8.4 Hz, 1 H), 8.06 (d, J=1.2 Hz, 1 H), 7.96 (s, 1 H), 7.49 (dd, J=1.6, 8.4 Hz, 1 H), 2.27 (s, 1 H), 1.30 (s, 9 H).

Aufarbeitung

  1. customThe ice bath was removed
  2. additionThe reaction was poured into ice (2000 g)
  3. customThe organic layer was separated
  4. extractionthe remaining aqueous layer was extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-330f892a6c10477cb7a801661cd8a01d
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973038B2

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