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1-Bromooctadecane → 15-Octadecyl-7,15-diazadispiro[5.1.5~8~.3~6~]hexadecane-14,16-dione

HRID 1706799
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1706799
[CH2:1]1[C:6]2([C:16](=[O:17])[NH:15][C:14](=[O:18])[C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>CO.CN(C=O)C.CCOCC>[CH2:38]([N:15]1[C:16](=[O:17])[C:6]2([CH2:5][CH2:4][CH2:3][CH2:2][CH2:1]2)[NH:7][C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C:14]1=[O:18])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21]
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Komponenten

7

Edukt 3

HCID 82181-BromooctadecaneHCID 14797Potassium HydroxideHCID 122347397,15-Diazadispiro[5.1.5.3]hexadecane-14,16-dione

Produkt 1

HCID 1853367615-Octadecyl-7,15-diazadispiro[5.1.5~8~.3~6~]hexadecane-14,16-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel
HCID 3283
Diethyl Ether
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 10.0 g. (0.04 moles) of 7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione in 150 ml of anhydrous methanol in a 500 ml flask was added 2.6 g. of 86% KOH (0.04 moles) and the mixture was shaken until solution was obtained. The reaction mixture was then evaporated to dryness under reduced pressure. The residue was transferred to a 300 ml 3-necked flask equipped with a stirrer, thermometer, condenser with drying tube, dropping funnel and nitrogen inlet with the aid of a small amount of dry DMF. To the potassium imide salt, under a nitrogen atmosphere, was added 150 ml of dry DMF. To the stirred solution was added dropwise a solution of 13.3 g. (0.04 moles) of n-octadecyl bromide in 50 ml of DMF. The reaction mixture was heated slowly to 75° C. and held at that temperature for 3 hours. The reaction mixture was cooled and allowed to stand at room temperature overnight. The reaction mixture was then taken up in 500 ml ether, the ether solution washed well with water, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue, which crystallized on standing, was recrystallized from methanol yielding 14.3 g. of white needles as the product, m.p. 39°-40° C.

Aufarbeitung

  1. customwas obtained
  2. customThe reaction mixture was then evaporated to dryness under reduced pressure
  3. customThe residue was transferred to a 300 ml 3-necked flask
  4. customequipped with a stirrer
  5. customthermometer, condenser with drying tube
  6. additionTo the potassium imide salt, under a nitrogen atmosphere, was added 150 ml of dry DMF
  7. additionTo the stirred solution was added dropwise a solution of 13.3 g
  8. temperatureThe reaction mixture was cooled
  9. waitto stand at room temperature overnight
  10. washthe ether solution washed well with water
  11. dry with materialdried over anhydrous Na2SO4
  12. customevaporated under reduced pressure
  13. customThe residue, which crystallized
  14. customwas recrystallized from methanol yielding 14.3 g

Quellen und Nachweise

ORD-Eintrag
ord-e42ddda7ea04449990de802ac060b4e0
Quelldatensatz
uspto-grants-1980_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04208522

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