Butylamine → Guanidine, pentabutyl-

HRID 654565

Reaktionsgleichung

Reaktionsgleichung von HRID 654565
[CH2:1]([N:5]([CH2:17][CH2:18][CH2:19][CH3:20])[C:6](=O)[N:7]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29]>C(#N)C>[CH2:1]([N:5]([CH2:17][CH2:18][CH2:19][CH3:20])[C:6](=[N:30][CH2:26][CH2:27][CH2:28][CH3:29])[N:7]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 8007ButylamineHCID 20691TetrabutylureaHCID 24813Phosphorus oxychloride

Produkt 1

HCID 189218Guanidine, pentabutyl-Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine.

Aufarbeitung

  1. customwhereupon a soft, fluffy precipitate formed
  2. temperatureThe mixture was warmed to 60° C. for one hour
  3. temperatureagain cooled to 0° C.
  4. customquenched with 50 ml
  5. extractionof 25% (by weight) aqueous sodium hydroxide solution and extracted with ether
  6. dry with materialThe ether extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customto give a pale yellow oil which
  9. distillationupon distillation

Quellen und Nachweise

ORD-Eintrag
ord-7f3eb4a7c91445d78532f762b1fbc41e
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05132423

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