Triethylamine → Ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate

HRID 606496Notes

Reaction equation

HRID 606496 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.Cl[C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[NH2:6][C:4]([C:3]1[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=1[NH:1][C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 27789392-Amino-6-fluorobenzamide

Product 1

HCID 66769038Ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-6-fluorobenzamide (3.80 g, 24.7 mmol) and triethylamine (2.99 g, 29.6 mmol) in THF (50 mL) was added dropwise ethyl chloroglyoxylate (3.70 g, 27.1 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was suspended in ethanol, and the insoluble material was collected by filtration to give ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate as a white powder (4.95 g, 79%).

Workup

  1. temperaturecooling
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe insoluble material was collected by filtration

Sources & evidence

ORD record
ord-4c7eea42828540638329d92148965f85
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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