Hydrochloric Acid → 1-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropane

HRID 342040

Reaktionsgleichung

Reaktionsgleichung von HRID 342040
[C-:1]#[N:2].[K+].[CH2:4]([NH2:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:12]([C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]1)=O.Cl>O.C(O)C>[CH2:4]([NH:11][CH:12]([C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]1)[C:1]#[N:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 9032Potassium CyanideHCID 9964122Ethyl 1-formylcyclopropanecarboxylate

Produkt 1

HCID 153910461-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropaneAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

An eggplant type flask was charged with 131 mg of potassium cyanide and 539 mg of benzylamine, and the contents were dispersed in 1 ml of water. Thereto was added dropwise 146 mg of ethyl 1-formylcyclopropane-1-carboxylate dissolved in 2 ml of ethanol at room temperature, followed by dropwise addition of 0.2 ml of concentrated hydrochloric acid. The reaction solution was stirred for 2.5 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and, after removing insoluble matter by filtration, concentrated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 231 mg (87%) of the title compound in the form of colorless oil.

Aufarbeitung

  1. customcompletion of the reaction
  2. extractionextracted with ethyl acetate
  3. washNext, the resulting organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter removing insoluble matter
  6. filtrationby filtration
  7. concentrationconcentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d89e0989ae9549d7814e916ed2e809d7
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856518

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