Acetic Acid → HCID 178511211, Verbindung

HRID 278524

Reaktionsgleichung

Reaktionsgleichung von HRID 278524
C([CH:3]=[CH2:4])=O.C([O:8][C:9](=[O:11])[CH3:10])(=O)C.C[P:13]([O:18]CC)(=O)OCC.[C-]#[N:22].[Na+].[Cl-].[NH4+].Cl.[C:27]([OH:30])(=O)C>N.C(O)C>[NH4+:22].[NH2:22][CH:10]([CH2:4][CH2:3][PH:13]([CH2:27][OH:30])=[O:18])[C:9]([O-:8])=[O:11]

Komponenten

10

Edukt 7

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7847AcroleinHCID 7918Acetic AnhydrideHCID 8929Sodium CyanideHCID 12685Diethyl methylphosphonateHCID 25517Ammonium Chloride

Produkt 1

HCID 178511211HCID 178511211, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 222AmmoniaLösungsmittelHCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

At room temperature, 5.61 g (0.10 mol) of freshly distilled acrolein are added to 10.21 g (0.10 mol) of acetic anhydride. At 25 to 30° C., this mixture is subsequently added dropwise to 13.61 g (0.10 mol) of diethyl methanephosphonate and 4.6 g (0.1 mol) of ethanol. The mixture is stirred at 30° C. for 2 hours and then, at 25 to 28° C., added dropwise to a solution of 4.9 g (0.10 mol) of sodium cyanide and 10.7 g (0.20 mol) of ammonium chloride in 50 ml of ammonia (25% strength). After 2 hours at 30° C., the crude aminonitrile is added dropwise to 200 ml of hydrochloric acid (37% strength). The mixture is subsequently heated under reflux for 2 hours, while ethanol and acetic acid are distilled off. The mixture is concentrated using a rotary evaporator, a pH of approximately 9 is set using ammonia solution and the product is purified by crystallization from methanol. This gives 19.6 g (99% of theory) of 2-amino-4-(hydroxymethylphosphinyl)-butyric acid, ammonium salt.

Aufarbeitung

  1. waitAfter 2 hours at 30° C.
  2. temperatureThe mixture is subsequently heated
  3. distillationare distilled off
  4. concentrationThe mixture is concentrated
  5. customa rotary evaporator
  6. customthe product is purified by crystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-b0e01c018bd44298af318637fdb4df3f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359162B1

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