Triethylamine → Ethyl ((2-(aminocarbonyl)-4-fluorophenyl)amino)(oxo)acetate

HRID 606479Notes

Reaction equation

HRID 606479 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][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.C(OCC)(=O)C>[NH2:6][C:4]([C:3]1[CH:7]=[C:8]([F:11])[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

6

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 102410032-Amino-5-fluorobenzamide

Product 1

HCID 66768981Ethyl ((2-(aminocarbonyl)-4-fluorophenyl)amino)(oxo)acetateYield 87.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-fluorobenzamide (2.00 g, 13.0 mmol) and triethylamine (1.45 g, 14.3 mmol) in THF (40 mL) was added dropwise ethyl chloroglyoxylate (1.95 g, 14.3 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was washed with ethanol to give ethyl ((2-(aminocarbonyl)-4-fluorophenyl)amino)(oxo)acetate as a white powder (2.88 g, 87%).

Workup

  1. temperaturecooling
  2. washwashed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with ethanol

Sources & evidence

ORD record
ord-f7a7079f6dda402e8eaed25a632e2472
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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