Sodium Hydroxide → Tert-butyl-3,3-dinitroazetidine

HRID 1171923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171923
Cl.[C:2]([N:6]1[CH2:9][C:8](CO)([N+:10]([O-:12])=[O:11])[CH2:7]1)([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[N:17]([O-:19])=[O:18].[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>O.[Fe-4](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].[K+]>[C:2]([N:6]1[CH2:7][C:8]([N+:10]([O-:12])=[O:11])([N+:17]([O-:19])=[O:18])[CH2:9]1)([CH3:3])([CH3:4])[CH3:5]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 62655Sodium PersulfateHCID 19010110N-tert-butyl-3-hydroxymethyl-3-nitroazetidine hydrochlorideHCID 23668193Sodium Nitrite

Produkt 1

HCID 10954639Tert-butyl-3,3-dinitroazetidineAusbeute 103,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178511492HCID 178511492, VerbindungKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution (60 ml) of N-tert-butyl-3-hydroxymethyl-3-nitroazetidine hydrochloride (13.50 g, 0.060 mol) prepared in the Example 3 in distilled water, 30 ml of aqueous solution of NaOH (7.173 g, 0.179 mol) was added. The resulting yellow solution was stirred for 3 hours at room temperature. The resultant was cooled to 8° C. and a chilled solution (45 ml) of sodium nitrite (NaNO2) (16.5 g, 0.239 mol) and potassium ferrocyanide (K3Fe(CN)6) (1.974 g, 0.060 mol) in distilled water was added slowly. Then, solid sodium persulphate (Na2S2O8) (17.80 g, 0.075 mol) was added in a single portion. The resulting yellow solution was warmed to room temperature as the solution gradually turned into light orange color. The solution was stirred for another 1 hour and then extracted with dichloromethane (CH2Cl2) (150 ml). The organic layer was dried with magnesium sulfate (MgSO4) and the solvent was removed via vacuum evaporation to give N-tert-butyl-3,3-dinitroazetidine (12.583 g, 0.062 mol, yield: 86.66%) as a yellow oil.

Aufarbeitung

  1. temperatureThe resultant was cooled to 8° C.
  2. temperatureThe resulting yellow solution was warmed to room temperature as the solution
  3. stirringThe solution was stirred for another 1 hour
  4. extractionextracted with dichloromethane (CH2Cl2) (150 ml)
  5. dry with materialThe organic layer was dried with magnesium sulfate (MgSO4)
  6. customthe solvent was removed via vacuum evaporation

Quellen und Nachweise

ORD-Eintrag
ord-5fe444eb79f642b6bad2631d1dbc467e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829729B2

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