Potassium Carbonate → 6-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-chloropyridin-2-amine

HRID 1050717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050717
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][CH2:9][CH3:10])=[CH:5][N:6]=1.Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([Cl:19])[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:19][C:14]1[N:13]=[C:12]([N:8]([CH2:7][C:4]2[S:3][C:2]([Cl:1])=[N:6][CH:5]=2)[CH2:9][CH3:10])[C:17]([Cl:18])=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 230162,3,6-TrichloropyridineHCID 22450338N-((2-Chlorothiazol-5-yl)methyl)ethanamine

Produkt 1

HCID 1178764726-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-chloropyridin-2-amineAusbeute 39,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

18.0 g of 2-chloro-5-ethylaminomethylthiazole, 18.6 g of 2,3,6-trichloropyridine, 30.0 g of potassium carbonate and 200 mL of N,N-dimethylformamide (DMF) were added in a 500 mL single neck flask equipped with a magnetic stirrer. After stirred at reflux temperature for 4 to 6 hours, the reaction mixture was extracted with ethyl acetate, the organic layer was separated while the aqueous layer was extracted with ethyl acetate twice. The organic phases were combined, and dried over anhydrous sodium sulfate after washed with an iced aqueous sodium chloride solution twice, then remove the solvent under reduced pressure to obtain 25.0 g of crude product which was purified by a silica gel column chromatography using a petroleum ether/ethyl acetate (20/1) as an eluent to obtain 13.0 g of 6-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-chloropyridin-2-amine, having the content 91.0%, as a yellow viscous liquid, and rod-like crystals were generated after standing, m.p.: 95.8-96.8 □ GC-MS (M+) (EI, 70 eV, m/z) calc: 321. found: 321. 1H NMR (CDCl3/TMS, 300 MHz) δ (ppm) 1.179 (t, J=7.2 Hz, 3H, CH3), 3.413 (q, J=7.2 Hz, 2H, CH2), 4.726 (s, 2H, CH2), 6.378 (d, J=8.7 Hz, 1H, Py H), 7.447 (d, J=8.7 Hz, 1H, Py H), 7.497 (s, 1H, Thiazole-H).

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. temperatureat reflux temperature for 4 to 6 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customthe organic layer was separated while the aqueous layer
  5. extractionwas extracted with ethyl acetate twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. washafter washed with an iced aqueous sodium chloride solution twice
  8. customremove the solvent under reduced pressure
  9. customto obtain 25.0 g of crude product which
  10. customwas purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-61dd6fbd659543a289d915f4b77e978e
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09386769B2

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