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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1717249Generated: October 26, 2026

Ethylamine → 4-azido-N-ethylbenzamide

https://huagongshe.com/reaction/1717249

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthylamineHCID 6341—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant4-Azidobenzoic acidHCID 3034184—
SolventTetrahydrofuranHCID 8028—
SolventTriethylamineHCID 8471—
Solventacetonitrile N,N-dimethylformamideHCID 21891449—
Product4-azido-N-ethylbenzamideHCID 5943222696%

Reaction Steps

To a solution of 4-azidobenzoic acid (0.65 g) in acetonitrile-DMF (2:1, 15 ml) were successively added 2M ethylamine in THF solution (2.4 ml), triethylamine (0.67 ml), HOBt (0.79 g) and WSC (0.92 g), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a pale-yellow powder (0.73 g, 96%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07803822B2
Source datasetuspto-grants-2010_09
ORD IDord-64f83f89ed7d4c429ddd0d2b6464814b
Source noteuspto-grants-2010_09