Water → Ethyl ((2-(aminocarbonyl)-4-iodophenyl)amino)(oxo)acetate

HRID 606476Notes

Reaction equation

HRID 606476 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I: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].O>C1COCC1>[NH2:6][C:4]([C:3]1[CH:7]=[C:8]([I: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 4

HCID 962WaterHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 208633Benzamide, 2-amino-5-iodo-

Product 1

HCID 66769092Ethyl ((2-(aminocarbonyl)-4-iodophenyl)amino)(oxo)acetateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-iodobenzamide (15.8 g, 60.3 mmol) and triethylamine (7.32 g, 72.4 mmol) in THF (300 mL) was added dropwise ethyl chloroglyoxylate (9.05 g, 66.3 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the precipitated insoluble material was collected by filtration. The solid was washed with water to give ethyl ((2-(aminocarbonyl)-4-iodophenyl)amino)(oxo)acetate as a white powder (20.9 g, 96%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was collected by filtration
  3. washThe solid was washed with water

Sources & evidence

ORD record
ord-0052164211744b3e8765ad2b98314498
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

Loading…