N-Hexadecylbenzamide

Benzoyl chloride (13.0 mL, 112 mmol) was dissolved in dichloromethane (200 mL). The solution was placed in an ice bath and cooled to 0 °C. A second solution of 1-hexadecylamine (1) (30.8 g, 110 mmol) and triethylamine (17.0 mL, 122 mmol) in dichloromethane (300 mL) was added dropwise under an NGeneral procedure: All compounds were synthesized by a one-step coupling reaction. Briefly, in a general procedure the appropriate acid (1 eq), and (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholino-carbenium hexafluoro phosphate (COMU, 1 eq) were dissolved in anhydrous CH2Cl2/CH3CN (3/1) at room temperature under a nitrogen atmosphere. After 10 min diisopropylethylamine (2 eq) was added and the resulting orange-red solution was stirred for 30 min. Hexadecylamine (1 eq) in CH3CN was then injected into the reaction mixture and vigorous stirring at room temperature was continued until TLC confirmed the completion of the reaction (1–6 h). The reaction mixture was diluted with CH2Cl2 and washed with 5percent HCl, saturated NaHCO3 and brine. The organic layers were collected, dried over anhydrous Na2SO4 and filtered. The solvent was evaporated under reduced pressure and crude purified by flash chromatography to give white solids and reaction yields range from 45percent to 85percent.

Molecular Weight:345.6
XLogP3:7.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:16
Exact Mass:345.303164868
Monoisotopic Mass:345.303164868
Topological Polar Surface Area:29.1
Heavy Atom Count:25
Complexity:297
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes