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Dicyclohexylcarbodiimide → HCID 19857803, Verbindung

HRID 1902220
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1902220
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([CH:21]([CH:25]([OH:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:22]([OH:24])=[O:23])[CH2:17][CH2:18][CH2:19][CH3:20].O[N:34]1[C:38](=[O:39])[CH2:37][CH2:36][C:35]1=[O:40]>COCCOC>[CH2:16]([CH:21]([CH:25]([OH:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:22]([OH:24])=[O:23])[CH2:17][CH2:18][CH2:19][CH3:20].[C:35]1(=[O:40])[NH:34][C:38](=[O:39])[CH2:37][CH2:36]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 19857780HCID 19857780, Verbindung

Produkt 1

HCID 19857803HCID 19857803, VerbindungAusbeute 104,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dicyclohexylcarbodiimide (27 g) dissolved in 1,2-dimethoxyethane (300 cc) is added, in the course of 40 minutes, to a solution, kept at 0° C., of 2-n-pentyl-3-hydroxynonanoic acid (29.1 g) and N-hydroxysuccinimide (14.1 g) in 1,2-dimethoxyethane (300 cc). The reaction mixture is stirred at 0° C. for 3 hours and then kept at 4° C. for 21 hours. The precipitate formed is filtered off and washed twice with 1,2-dimethoxyethane (100 cc in total). The filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C. The concentrate is taken up in a mixture of diisopropyl ether (300 cc) and acetic acid (3 cc). After standing for 2 hours at 20° C., the precipitate formed is filtered off and washed twice with diisopropyl ether (40 cc in total). The filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C. Succinimide 2-n-pentyl-3-hydroxynonanoate (42.6 g) is thus obtained in the form of a yellow oil.

Aufarbeitung

  1. additionis added, in the course of 40 minutes, to a solution
  2. waitkept at 4° C. for 21 hours
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washwashed twice with 1,2-dimethoxyethane (100 cc in total)
  6. concentrationThe filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C
  7. additionThe concentrate is taken up in a mixture of diisopropyl ether (300 cc) and acetic acid (3 cc)
  8. waitAfter standing for 2 hours at 20° C.
  9. customthe precipitate formed
  10. filtrationis filtered off
  11. washwashed twice with diisopropyl ether (40 cc in total)
  12. concentrationThe filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-6cae515619a748c8921fbbabb2e435bf
Quelldatensatz
uspto-grants-1982_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04362716

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