Water → 2-cyano-N-cyclopropylacetamide

HRID 279731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279731
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([CH2:7][C:8](O)=[O:9])#[N:6].C(N=C=NC(C)C)(C)C.O>O1CCCC1.CC#N>[CH:1]1([NH:4][C:8](=[O:9])[CH2:7][C:5]#[N:6])[CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 9740Cyanoacetic acidHCID 12734DiisopropylcarbodiimideHCID 69828Cyclopropylamine

Produkt 1

HCID 21678842-cyano-N-cyclopropylacetamideAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Cyclopropylamine (5.0 grams, 88 mmole) was combined with 7.5 grams (g) (88 mmol) of cyanoacetic acid in 50 milliliters (ml) tetrahydrofuran (THF) and 50 ml CH3CN. Diisopropylcarbodiimide (20 g, 97 mmol) dissolved in 10 ml THF was added dropwise. The reaction mixture exothermed and a white precipitate formed. The mixture was stirred at 20° C. for 20 hours, 5 ml water was added and the reaction mixture was stirred another 5 minutes. The precipitate was filtered off and the filtrate evaporated giving a white solid which was then recrystallized to yield 9.2 g (74 mmol) of N-(cyclopropyl)-2-cyanoacetamide, a white solid (m.p. 104°-106° C.) (84% yield).

Aufarbeitung

  1. additionwas added dropwise
  2. customa white precipitate formed
  3. stirringthe reaction mixture was stirred another 5 minutes
  4. filtrationThe precipitate was filtered off
  5. customthe filtrate evaporated
  6. customgiving a white solid which
  7. customwas then recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-88e8655de7aa40379f5b7919c56a9195
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04586954

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