Sodium hydride → tert-Butyl ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoylmalonate

HRID 1395727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1395727
[C:1]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl.[F:17][C:18]([F:45])([F:44])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1>COCCOC>[F:17][C:18]([F:44])([F:45])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[O:40])=[CH:37][CH:36]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 205493174-[15-(Trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride

Produkt 1

HCID 20549324tert-Butyl ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoylmalonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel3×

Versuchsvorschrift

A solution of 28.0 g. of tert-butyl ethyl malonate in 10 ml. of 1,2-dimethoxyethane is added to a suspension of 4.0 g. of sodium hydride in 1,2-dimethoxyethane under argon. A solution of 17.3 g. of 4-[15-(trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 5 hours, cooled, poured on ice and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to dryness. The residue is then recrystallized from ether to yield the product.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. temperaturecooled
  3. additionpoured on ice
  4. extractionextracted with ether
  5. washThe ether solution is washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue is then recrystallized from ether
  9. customto yield the product

Quellen und Nachweise

ORD-Eintrag
ord-a8dba90416f1418ba41cc485b32f326b
Quelldatensatz
uspto-grants-1980_05
Patentnummer
US04205085

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