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

HRID 2095802Notes

Reaction equation

HRID 2095802 reaction equation
[Br: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>[Br: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 757711-HydroxybenzotriazoleHCID 2428732-Bromo-4-fluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 28939521N-(2-bromo-4-fluorophenyl)-2-cyanoacetamideYield 59.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromo-4-fluoroaniline (10.0 g, 52.6 mmol), cyanoacetic acid (5.36 g, 63.1 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide•hydrochloride (15.1 g, 78.9 mmol), 1H-1,2,3-benzotriazol-1-ol (10.6 g, 78.9 mmol), triethylamine (10.9 mL, 78.9 mmol) and N,N-dimethylformamide (150 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 pad packed with NH silica gel. The solvent was evaporated under reduced pressure, and the obtained residue was washed with hexane and collected by filtration to give the title compound (8.04 g, 59%) 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 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-05c2708e80154c9692be3bf72e1b6c24
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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