Caprolactam → 2H-Azepin-2-one, hexahydro-N-lauroyl-

HRID 476820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 476820
[H-].[Na+].[NH:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:10].[C:11](Cl)(=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[C:11]([N:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:10])(=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 7768CaprolactamHCID 8166Dodecanoyl chlorideHCID 24758Sodium hydride2×

Produkt 1

HCID 217132H-Azepin-2-one, hexahydro-N-lauroyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Versuchsvorschrift

Sodium hydride [5.14 g (50% oil dispersion); 0.107 mol] in 100 ml of dry toluene was added to a 500 ml, 3-necked flask fitted with a mechanical stirrer. Azacycloheptan-2-one (10.07 g; 0.089 mol) was dissolved in 50 ml of dry toluene with slight warming and added to the sodium hydride suspension dropwise at room temperature. The suspension was stirred at room temperature for 1 hour. n-Dodecanoyl chloride (19.39 g; 0.089 mol) in 10 ml of dry toluene was added dropwise to the mixture and after the addition was complete, the mixture was stirred overnight at room temperature. The mixture was then washed with water, and the organic layer separated, dried with MgSO4, and concentrated. The resulting yellow oil was distilled 160° C./0.35 mm to yield 1-n-dodecanoylazacycloheptan-2-one as clear oil.

Aufarbeitung

  1. customfitted with a mechanical stirrer
  2. temperaturewith slight warming
  3. additionafter the addition
  4. stirringthe mixture was stirred overnight at room temperature
  5. washThe mixture was then washed with water
  6. customthe organic layer separated
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated
  9. distillationThe resulting yellow oil was distilled 160° C./0.35 mm

Quellen und Nachweise

ORD-Eintrag
ord-5012b362bf294a969c10d91a923bcbd3
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886545

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