ChemicalBook CAS DataBase List N,N-DIETHYLNICOTINAMIDE

N,N-DIETHYLNICOTINAMIDE synthesis

13synthesis methods

Product Name:N,N-DIETHYLNICOTINAMIDE
CAS Number:59-26-7
Molecular formula:C10H14N2O
Molecular Weight:178.23

626-55-1 Synthesis

626-55-1
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201230-82-2 Synthesis

201230-82-2
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109-89-7
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$10.00/5g

59-26-7
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$40.00/500mg

Yield:59-26-7 92%

Reaction Conditions:

with (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate;palladium diacetate;triethylamine in N,N-dimethyl-formamide at 20 - 60; under 2068.65 Torr; for 24 h;Inert atmosphere;Autoclave;chemoselective reaction;

Steps:

Carbonylative Amidation; General Procedure

General procedure: 5′-O-(4,4′-Dimethoxytrityl)-5-iodo-2′-deoxyuridine (5′-O-DMT-5-IdU) (1a) (1.0 mmol, 656mg), the corresponding amine 2 (2.0 mmol), Pd(OAc)2 (2 mol%), PTABS ligand (4 mol%), Et3N (10 mmol) and N2-purged DMF (10 mL) were added to a 100 mL stainless steel autoclave reaction flask at room temperature. The autoclave was closed and flushed with nitrogen gas and then pressurized with CO gas (40 psi). Caution. Carbon monoxide (CO) is an odorless, colorless and highly toxic gas. The reactions should be carried out in efficient fume hoods fitted with CO detectors. The reaction mixture was stirred with a mechanical stirrer (500 rpm) and heated at 60 °C for 24 h. The mixture was then allowed to cool to room temperature and the CO was vented carefully in a fume hood by adding KMnO4 solution. The reaction mass was diluted in cold water and subsequently extracted with EtOAc (3 × 25 mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. A slurry was prepared from the residue using silica gel and the product was isolated by column chromatography (60-120 neutralized silica gel; CHCl3/MeOH/Et3N, 97.5:2.0:0.5).

References:

Bhanage, Bhalchandra M.;Bhilare, Shatrughn;Gaikwad, Vinayak;Gupta, Gaurav;Kapdi, Anant R.;Sanghvi, Yogesh S.;Shah, Jagrut [Synthesis,2019,vol. 51,# 22,p. 4239 - 4248] Location in patent:supporting information

59-67-6 Synthesis