Potassium Hydroxide → HCID 16726889, Verbindung

HRID 425771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425771
[ClH:1].[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]#[N:17])=[CH:6][CH:5]=1.[OH-:18].[NH4+].[OH-].[K+]>O.C(Cl)Cl>[ClH:1].[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([C:16]([NH2:17])=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 236558594'-(Aminomethyl)[1,1'-biphenyl]-2-carbonitrile--hydrogen chloride (1/1)

Produkt 1

HCID 16726889HCID 16726889, VerbindungAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
72.5 °C

Versuchsvorschrift

4-Aminomethyl-2′-cyanobiphenyl hydrochloride (XVII) (100 g, 0.408 mole) was suspended in a mixture of water (500 ml) and methylene chloride (200 ml) at 25-30° C. and adjusted the pH to 9.0-9.5 with ammonium hydroxide (65 ml, 20% w/w) at 25-30° C. to get a clear solution. Organic layer was separated, washed with water (100 ml) and dried over sodium sulfate. Thereafter, organic layer was concentrated at below 60° C. and tert.butanol (300 ml) was added to the residue. The reaction mass was heated to 70-75° C. Thereafter, powdered potassium hydroxide (32.35 g, 0.491 mole) was added and heated to reflux for completion of the reaction. Water (400 ml) was added and aqueous layer was separated and extracted with methylene chloride (500 ml). The combined organic layer was washed with water (200 ml) and dried over sodium sulfate. Methylene chloride solution was cooled to 2-5° C. and the pH adjusted to 1.2-1.4 with hydrochloric acid. The precipitated product was stirred for one hour and filtered, washed with methylene chloride to afford the title compound as white powder (90 g, 84.1% yield).

Aufarbeitung

  1. customat 25-30° C.
  2. customto get a clear solution
  3. customOrganic layer was separated
  4. washwashed with water (100 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationThereafter, organic layer was concentrated at below 60° C.
  7. additiontert.butanol (300 ml) was added to the residue
  8. temperatureheated
  9. temperatureto reflux for completion of the reaction
  10. customaqueous layer was separated
  11. extractionextracted with methylene chloride (500 ml)
  12. washThe combined organic layer was washed with water (200 ml)
  13. dry with materialdried over sodium sulfate
  14. temperatureMethylene chloride solution was cooled to 2-5° C.
  15. filtrationfiltered
  16. washwashed with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-0a8955554706472095e2a500951e9319
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106216B2

Notizen zur Reaktion

Wird geladen…