Ethoxalyl chloride → HCID 178470313, compound

HRID 902879Notes

Reaction equation

HRID 902879 reaction equation
Cl[C:2](=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:9][C:10]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13]>N1C=CC=CC=1>[Cl:19][C:16]1[CH:15]=[C:11]2[C:10](=[CH:18][CH:17]=1)[NH:9][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:14][C:12]2=[O:13]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 788762-Amino-5-chlorobenzamide

Product 1

HCID 178470313HCID 178470313, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chlorooxoacetate (2.0 ml) was added to a solution of 2-amino-5-chlorobenzamide (2.50 g) in pyridine (15 ml), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resultant residue was dissolved in acetic acid (50 ml). Acetic anhydride (5.0 ml) was added to the solution, and the mixture was heated under reflux for 16 hours. The solvent was distilled off under reduced pressure, and ethanol was added to the residue. Crystals deposited were collected by filtration and washed to obtain the title compound (2.71 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resultant residue was dissolved in acetic acid (50 ml)
  3. additionAcetic anhydride (5.0 ml) was added to the solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 16 hours
  6. distillationThe solvent was distilled off under reduced pressure, and ethanol
  7. additionwas added to the residue
  8. filtrationCrystals deposited were collected by filtration
  9. washwashed

Sources & evidence

ORD record
ord-92d8f7b5a8f04602aea18b27a6cc1d52
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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