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

HRID 606483Notes

Reaction equation

HRID 606483 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.Cl[C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>C1COCC1>[NH2:6][C:4]([C:3]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:2]=1[NH:1][C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 203382172-Amino-5-methoxybenzamide

Product 1

HCID 66768932Ethyl ((2-(aminocarbonyl)-4-methoxyphenyl)amino)(oxo)acetateYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-methoxybenzamide (1.50 g, 9.03 mmol) and triethylamine (1.00 g, 9.93 mmol) in THF (40 mL) was added dropwise ethyl chloroglyoxylate (1.36 g, 9.93 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 filtered cake was washed with water and ethanol to give ethyl ((2-(aminocarbonyl)-4-methoxyphenyl)amino)(oxo)acetate as a pale-yellow powder (2.42 g, 100%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was collected by filtration
  3. washThe filtered cake was washed with water and ethanol

Sources & evidence

ORD record
ord-cda0f49760e945e0b28577ca492f9029
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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