Sodium hydride → 1-Ethyl-4-imidazolin-2-one 3-alpha-ethyltetradecanoate

HRID 231281

Reaktionsgleichung

Reaktionsgleichung von HRID 231281
[CH2:1]([N:3]1[CH:7]=[CH:6][NH:5][C:4]1=[O:8])[CH3:2].ClC([O:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])C.[H-].[Na+]>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH2:1]([N:3]1[CH:7]=[CH:6][NH:5][C:4]1=[O:8])[CH3:2].[CH2:1]([CH:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][C:13]([O-:12])=[O:27])[CH3:2]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 140652901-ethyl-1,3-dihydro-2H-imidazol-2-oneHCID 142456981-Chloroethyltetradecanoate

Produkt 1

HCID 867432111-Ethyl-4-imidazolin-2-one 3-alpha-ethyltetradecanoateAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

1-Ethyl-4-imidazolin-2-one (1 gm, 0.009 mol) and 1-chloroethyltetradecanoate (2.6 gm, 0.009 mol) were dissolved in 13 ml of dry chloroform and a suspension of sodium hydride in dry benzene (3 ml) was added portionwise. The reaction mixture was stirred at room temperature overnight and was followed by the workup presented in the preceeding examples. After purification by liquid chromatography using silica gel as the supporting material and chloroform as the eluant (EM Silica gel 500 G, 60-200 mesh was used), 1-ethyl-4-imidazolin-2-one-3-α-ethyltetradecanoate was obtained in a yield of 10% (350 mg). 1H n.m.r.(CC14): δ0.90(3H, t, J=5 Hz, CH3 [CH2 ]11CH2 --); 1.28(22H, s, broad, CH3 [CH2 ]11CH2 --); 1.30(3H, t, J=7 Hz, CH3CH2N--); 1.61(3H, d, J=6 Hz, --CHCH3 --); 2.25(2H, t, J=6 Hz, CH3 [CH2 ]10CH2 --); 3.60(2H, q, J=6 Hz, CH3CH2N--); 6.10(1H, d, J=3 Hz, HC=CH); 6.23(1H, d, J=3 Hz, HC=CH); 6.43(1H, q, J=6 Hz, CH3CH--). νmax (film): 3200, 3180(HC=CH), 1745, 1705, 1690(C=O); 1250 cm-1 (C-O-C). m/e+1 367, C21H38N2O3 requires 366.

Aufarbeitung

  1. additionwas added portionwise
  2. customAfter purification by liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-65f181d65017461e9db482bd41ec9c6f
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845233

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