Ethylamine → 4-azido-N-ethylbenzamide

HRID 1717249Notes

Reaction equation

HRID 1717249 reaction equation
[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:13]([NH2:15])[CH3:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.C1COCC1.C(N(CC)CC)C>[N:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:15][CH2:13][CH3:14])=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

8

Reactant 4

HCID 6341EthylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 30341844-Azidobenzoic acid

Product 1

HCID 594322264-azido-N-ethylbenzamideYield 96%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

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%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-64f83f89ed7d4c429ddd0d2b6464814b
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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