ChemicalBook CAS DataBase List N,N,N',N'-TETRAETHYLMALONAMIDE

N,N,N',N'-TETRAETHYLMALONAMIDE synthesis

9synthesis methods

Product Name:N,N,N',N'-TETRAETHYLMALONAMIDE
CAS Number:33931-42-9
Molecular formula:C11H22N2O2
Molecular Weight:214.3

141-82-2 Synthesis

141-82-2
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109-89-7
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33931-42-9
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$12.00/250mg

Yield: 86%

Reaction Conditions:

with benzotriazol-1-ol;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;triethylamine in chloroform at 20; for 18 h;

Steps:

2.2 Ligand Synthesis
General procedure: TEMA and TEDGA syntheses were carried out and supplied by Reading University,UK. TEMA was synthesized by the addition of 2 mol. equivalents of hydroxybenzotriazole(HOBt), triethylamine, diethylamine and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidehydrochloride (EDC·HCl) to a suspension of malonic acid in chloroform. TEDGA wassynthesized by the addition of 2 mol. equivalents of HOBt, triethylamine, diethylamineand EDC·HCl to a suspension of 2,2′-oxydiacetic acid in chloroform. Both reactions werestirred at room temperature for 18 h. The crude reactions were washed with 1 mol·L-1 HCland 1 mol·L-1 NaOH. The combined organic layers were separately dried over MgSO4,filtered, and the solvent was removed under reduced pressure. The TEMA yield was86%. The TEDGA yield was 95%. TEMA 1H NMR (400 MHz, CDCl3)δ 3.46-3.37 (m,10H), 1.20 (t, J = 6.8 Hz, 6H), 1.14 (t, J = 7.2 Hz, 6H); 13C NMR (101 MHz, CDCl3)δ166.4, 42.6, 40.6, 40.3, 14.1, 12.8; (FTMS + pESI) calculated: C11H22N2Na[M+Na]+:237.1573 g·mol-1; observed: 237.1578 g·mol-1.

References:

Canner, Adam J.;Harwood, Laurence M.;Cowell, Joseph;Babra, Jasraj S.;Brown, Solomon F.;Ogden, Mark D. [Journal of Solution Chemistry,2020,vol. 49,# 1,p. 52 - 67]