5-Bromopentanenitrile → HCID 54220720, Verbindung

HRID 543783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543783
NC1N=CNN=1.C[O-].[Na+].BrCCCCC#N.[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH:27]=[N:26][C:25]([NH2:28])=[N:24]1)#[N:18].[F:29][C:30]([F:36])([F:35])[CH2:31][N:32]=[C:33]=[S:34]>CO.C(#N)C>[F:29][C:30]([F:36])([F:35])[CH2:31][NH:32][C:33](=[S:34])[NH:28][C:25]1[N:26]=[CH:27][N:23]([CH2:22][CH2:21][CH2:20][CH2:19][C:17]#[N:18])[N:24]=1

Komponenten

8

Edukt 5

HCID 794355-BromopentanenitrileHCID 10942334Sodium MethoxideHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 21279827HCID 21279827, VerbindungHCID 178418311HCID 178418311, Verbindung

Produkt 1

HCID 54220720HCID 54220720, VerbindungAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Amino-1,2,4-triazole (4.2 g.) was added to a solution of sodium methoxide in MeOH (1.2 g. sodium in 30 ml. MeOH) and the solution stirred for 0.5 hours at room temperature. 5-Bromovaleronitrile (8.1 g.) was added and the solution heated under reflux for 12 hours. The solution was evaporated and the residue partitioned between water and EtOAc. The extracts were washed with brine, dried over MgSO4 and evaporated to give a pale yellow oil (6.5 g.) which was purified by medium pressure liquid chromatography using EtOAc/MeOH 6:1 v/v as eluant. The colourless oil obtained was used without characterisation for the following reaction. The crude 1-(4-cyanobutyl)-3-amino-1,2,4-triazole (5.45 g.) in acetonitrile (80 ml.) was treated with 2,2,2-trifluoroethylisothiocyanate (4.4 g.) and the solution heated under reflux for 3.5 hours. Evaporation gave a white sticky solid which was triturated with ether/EtOH to give 5-(3-[3-(2,2,2-trifluoroethyl)thioureido]-1,2,4-triazol-1-yl)valeronitrile (4.04 g.) as a white solid, m.p. 136°-138°.

Aufarbeitung

  1. temperaturethe solution heated
  2. temperatureunder reflux for 12 hours
  3. customThe solution was evaporated
  4. customthe residue partitioned between water and EtOAc
  5. washThe extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a pale yellow oil (6.5 g.) which
  9. customwas purified by medium pressure liquid chromatography
  10. customThe colourless oil obtained
  11. customwas used without characterisation for the following reaction
  12. temperaturethe solution heated
  13. temperatureunder reflux for 3.5 hours
  14. customEvaporation
  15. customgave a white sticky solid which
  16. customwas triturated with ether/EtOH

Quellen und Nachweise

ORD-Eintrag
ord-18b9abc2cb3746418d5435e4e18194e3
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04447441

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