Ethanol → Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

HRID 1713064

Reaktionsgleichung

Reaktionsgleichung von HRID 1713064
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[SH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].CCO>O>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 810792-Chloronicotinonitrile

Produkt 1

HCID 738459Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-3-cyanopyridine (330 g, 2.38 mol), ethyl 2-mercaptoacetate (361.2 g, 3.01 mol), sodium carbonate (265 g, 2.5 mol) and EtOH (1.2 l) was heated to reflux for 4.5 h. The reaction mixture was then cooled to ambient temperature and added to water (15 l). The resulting slurry was stirred for 0.5 h then filtered. The filter cake was washed with two portions of water (2×2.5 l). The solids were then dried to constant weight under vacuum at 45° C. to yield the title compound as a brown solid (493 g, 93%). δH (CDCl3) 8.68 (1H, dd, J 4.7, 1.2 Hz), 7.93 (1H, dd, J 8.5, 1.2 Hz), 7.29 (1H, dd, J 8.5, 4.7 Hz), 5.90 (2H, br), 4.38 (2H, q, J 7.0 Hz), 1.40 (3H, t, J 7.0 Hz). LCMS RT 2.9 minutes, 223 (M+H)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 h
  3. filtrationthen filtered
  4. washThe filter cake was washed with two portions of water (2×2.5 l)
  5. customThe solids were then dried to constant weight under vacuum at 45° C.

Quellen und Nachweise

ORD-Eintrag
ord-754035339ba0479390b91ed3f2896832
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795256B2

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