Ethoxalyl chloride → HCID 178470313, compound

HRID 2104406Notes

Reaction equation

HRID 2104406 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 away under reduced pressure, and ethanol was added to the residue. Crystals precipitated were collected by filtration and washed, to thereby give 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 away under reduced pressure, and ethanol
  7. additionwas added to the residue
  8. customCrystals precipitated
  9. filtrationwere collected by filtration
  10. washwashed

Sources & evidence

ORD record
ord-bf146de2decb4c2993a058fcfa24abd2
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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