Nitrite → Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine

HRID 1942393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942393
Br.Br.[CH2:3]([NH:6][CH:7]1[CH2:16][CH2:15][C:10]2[N:11]=[C:12](N)[S:13][C:9]=2[CH2:8]1)[CH2:4][CH3:5].N([O-])=O.P(P(O)(O)=O)(O)(O)=O.[OH-].[Na+]>Cl>[CH2:3]([NH:6][CH:7]1[CH2:16][CH2:15][C:10]2[N:11]=[CH:12][S:13][C:9]=2[CH2:8]1)[CH2:4][CH3:5]

Komponenten

6

Edukt 4

HCID 946NitriteHCID 14798Sodium HydroxideHCID 24536Hypophosphoric acidHCID 86651296N6-propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine dihydrobromide

Produkt 1

HCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a solution of 14.5 g (38.9 mmol) N6-propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine dihydrobromide in 220 mL concentrated aqueous hydrochloric acid at −30° C. is drop wise added 66.3 mL of an aqueous 1N solution nitrite over the course of 30 minutes. After further stirring for 1 hour at the same temperature 5.44 ml (52.5 mmol) of a 50% aqueous solution hypophosphoric acid is added. The reaction mixture is stored at 4° C. overnight. After having cooled down the solution again to −30° C. the mixture is slowly basified with 40% aqueous sodium hydroxide solution while temperature is kept at −30° C. The resulting mixture is warmed up to room temperature and extracted with chloroform/ethanol 5:1 (3×250 mL). The solution is dried over anhydrous sodium sulfate and concentrated in vacuum. The brown oil obtained is chromatographed over silica gel, eluting with dichloromethane/methanol 97:3 under ammonia atmosphere.

Aufarbeitung

  1. customat −30° C.
  2. customover the course of 30 minutes
  3. additionis added
  4. customis kept at −30° C
  5. temperatureThe resulting mixture is warmed up to room temperature
  6. extractionextracted with chloroform/ethanol 5:1 (3×250 mL)
  7. dry with materialThe solution is dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuum
  9. customThe brown oil obtained
  10. customis chromatographed over silica gel
  11. washeluting with dichloromethane/methanol 97:3 under ammonia atmosphere

Quellen und Nachweise

ORD-Eintrag
ord-d7c2c70224064ebb872f9ccdc888af4b
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389555B2

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