Triethylamine → N-(2-chloro-4-fluorophenyl)-2-cyanoacetamide

HRID 2095799Notes

Reaction equation

HRID 2095799 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]([CH2:12][C:13](O)=[O:14])#[N:11].CN(C)CCCN=C=NCC.Cl.N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:13](=[O:14])[CH2:12][C:10]#[N:11]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 3644962N-(2-chloro-4-fluorophenyl)-2-cyanoacetamideYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-4-fluoroaniline (3.55 g, 24.3 mmol), cyanoacetic acid (2.48 g, 29.2 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide•hydrochloride (7.01 g, 36.5 mmol), 1H-1,2,3-benzotriazol-1-ol (4.94 g, 36.5 mmol), triethylamine (5.10 mL, 36.5 mmol) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 16 hr. The mixture was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and filtered through a basic silica gel pad. The solvent was evaporated under reduced pressure, and the obtained residue was washed with hexane and collected by filtration to give the title compound (2.84 g, 54%) as a white solid.

Workup

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered through a basic silica gel pad
  4. customThe solvent was evaporated under reduced pressure
  5. washthe obtained residue was washed with hexane
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2cbd6a2d32d94a978ef05bae026b8dee
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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