Triethylamine → N-[(4-Cyanophenyl)methyl]nonanamide

HRID 2413761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2413761
[NH2:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(Cl)(Cl)Cl>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][NH:1][C:18](=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:4][CH:5]=1)#[N:8]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 69819Nonanoyl chlorideHCID 826084-(Aminomethyl)benzonitrile

Produkt 1

HCID 15725465N-[(4-Cyanophenyl)methyl]nonanamideAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a solution of 4-(aminomethyl)benzonitrile (5.0 g, 0.038 moles) in 100 mL chloroform is added 3.82 g (0.038 moles) triethylamine. A solution of nonanoyl chloride (6.68 g, 0.038 moles) in 10 mL chloroform is then added dropwise with stirring over a 10 min period and the final mixture stirred at room temperature for 18 hrs. The mixture is extracted with water (100 mL), saturated NaHCO3 (50 mL), 2N HCl (50 mL), dried over Na2SO4 and evaporated to leave 10.2 g crude N-(4-cyanobenzyl)nonanamide. This crude product is taken up in 50 mL dimethylformamide, to which is added 2.47 g (0.038 moles) sodium azide and 2.03 g (0.038 moles) ammonium chloride. The final mixture is heated at 90°-110° C. for 4 hrs after cooling, the mixture is diluted with water (350 mL) and the resultant precipitate recovered by suction filtration, washed with water, and vacuum dried. Recrystallization from ethyl acetate left N-[[4-(1H-tetrazol-5-yl)phenyl]methyl]nonanamide (2.6 g), m.p. 185°-187° C.

Aufarbeitung

  1. extractionThe mixture is extracted with water (100 mL), saturated NaHCO3 (50 mL), 2N HCl (50 mL)
  2. dry with materialdried over Na2SO4
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c42917e5c1aa42b2b91e9b3c3f2820f4
Quelldatensatz
uspto-grants-1988_01
Patentnummer
US04719232

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