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Water → Ethyl 7-{[4-(acetyloxy)nonyl](cyano)amino}heptanoate

HRID 1729911
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1729911
[H-].[Na+].[NH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]#[N:5].Cl[CH2:18][CH2:19][CH2:20][CH:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>C1C=CC=CC=1.CN(C)C=O>[C:28]([O:27][CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19][CH2:18][N:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]#[N:5])(=[O:30])[CH3:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 131047161-Chloro-4-acetoxynonaneHCID 21501476Ethyl 7-(cyanoamino)heptanoate

Produkt 1

HCID 71444712Ethyl 7-{[4-(acetyloxy)nonyl](cyano)amino}heptanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
2×
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (57%, in mineral oil) (0.48 g., 0.01 mole) is washed twice with benzene then suspended in benzene (50 ml.) and dimethylformamide (50 ml.). Ethyl 7-cyanamidoheptanoate (1.98 g. 0.01 mole) (Example N, Step 2) is added and the suspension heated on the steam bath for 15 minutes. The reaction mixture is cooled to room temperature, 1-chloro-4-acetoxynonane (2.6 g., 0.01 mole) (Example A, Step 3) is added and then the reaction is heated on the steam bath for 2 hours then stirred 18 hours at room temperature. The reaction is poured into water (300 ml.) and extracted with benzene (3 × 100 ml.). The benzene is washed with brine then dried over sodium sulfate. Removal of the solvent yields an oil which is purified by silica gel chromatography, elution solvent 3% methanol in chloroform, evaporation of the appropriate fraction affords ethyl 7-[N-(4-acetoxynonyl) cyanamido]-heptanoate. The yield is 3.2 g. (83 %).

Aufarbeitung

  1. temperaturethe suspension heated on the steam bath for 15 minutes
  2. temperaturethe reaction is heated on the steam bath for 2 hours
  3. extractionextracted with benzene (3 × 100 ml.)
  4. washThe benzene is washed with brine
  5. dry with materialthen dried over sodium sulfate
  6. customRemoval of the solvent
  7. customyields an oil which
  8. customis purified by silica gel chromatography, elution solvent 3% methanol in chloroform, evaporation of the appropriate fraction

Quellen und Nachweise

ORD-Eintrag
ord-7f39267595ec464295f68f56c928d005
Quelldatensatz
uspto-grants-1976_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03989749

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