Ammonia → N-(10-Undecenyl)homophthalimide

HRID 361478

Reaktionsgleichung

Reaktionsgleichung von HRID 361478
C(O)(=O)CC1C(=CC=CC=1)C(O)=O.NC(N)=O.N.[C:19]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]2[CH2:20]1.[H-].[Na+].Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44]>CS(C)=O.O.CO>[CH2:44]([N:24]1[C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]2[CH2:20][C:19]1=[O:30])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=[CH2:34]

Komponenten

10

Edukt 6

HCID 222AmmoniaHCID 1176UreaHCID 24758Sodium hydrideHCID 66643Homophthalic acidHCID 28414811-Bromo-1-undeceneHCID 3494351,3(2H,4H)-isoquinolinedione2×

Produkt 1

HCID 23295912N-(10-Undecenyl)homophthalimideAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

This example illustrates a synthesis of N-(10,11-Oxidoundecyl)homophthalimide (inventive compound no. 1114). A mixture of homophthalic acid (54.0 g; 0.3 mole) and finely powdered urea (19.82 g; 0.33 mole) were heated to 175-185° C. until no more ammonia evolves, evidenced by pH paper. The crude product was refluxed with methanol (500 mL) and homophthalimide isolated by filteration (29 g; 60%). Sodium hydride(95%) (576 mg, 24 mmol) was added to a solution of homophthalimide (3.2 g, 20 mmol) in anhydrous dimethylsulfoxide (75 mL). After 20 minutes of stirring, 1-bromoundec-10-ene (5.6 g, 24 mmol) was added. After 16 hours of stirring at room temperature, the reaction mixture was poured into a separatory funnel containing 500 mL of water and extracted with ethyl acetate (3×100 mL). The organic extracts were combined, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using petroleum ether/5% ethyl acetate eluant to yield 2.2 g (35.5% yield) N-(10-Undecenyl)homophthalimide.

Aufarbeitung

  1. customisolated by filteration (29 g; 60%)
  2. stirringAfter 16 hours of stirring at room temperature
  3. additionthe reaction mixture was poured into a separatory funnel
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washwashed with water (100 mL) and brine (100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product obtained
  9. customwas further purified by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ba7eb8b7873b43cfb85b259eb05a74a5
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

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