Nicotinic Acid → 2-(3-Pyridyl)benzothiazole

HRID 1287829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1287829
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9](O)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1>C(Cl)(Cl)Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:9]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:11]=1

Komponenten

4

Edukt 2

HCID 938Nicotinic AcidHCID 87132-Aminothiophenol

Produkt 1

HCID 2359222-(3-Pyridyl)benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

o-Aminothiophenol 36.9 g (0.30 mole) and nicotinic acid 55.5 g (0.45 mole) are dissolved in 600 cc of chloroform and 360 g of polyphosphoric acid ethyl ester (PPE). The resulting solution is heated at reflux for 1 hour. It is then concentrated to dryness. The residue is poured onto 1500 cc of ice-water, and the resulting mixture is brought to pH 10 with 50% NaOH solution. The aqueous mixture is extracted with CHCl3, and the extracts dried (MgSO4), filtered, and concentrated in vacuo. The residue is recrystallized from acetonitrile to yield the title A compound (42.8 g, 68%, of theory).

Aufarbeitung

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux for 1 hour
  3. concentrationIt is then concentrated to dryness
  4. additionThe residue is poured onto 1500 cc of ice-water
  5. extractionThe aqueous mixture is extracted with CHCl3
  6. dry with materialthe extracts dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is recrystallized from acetonitrile
  10. customto yield the title A compound (42.8 g, 68%, of theory)

Quellen und Nachweise

ORD-Eintrag
ord-aaa49fdb4a1947e99981509e25dbf2e4
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03985885

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