Chloroacetyl chloride → 5-Chloro-2-((2-chloroacetyl)amino)benzoic acid

HRID 1626757

Reaction equation

HRID 1626757 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][CH2:13][C:14](Cl)=[O:15]>C1(C)C=CC=CC=1>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][C:14](=[O:15])[CH2:13][Cl:12])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 124762-Amino-5-chlorobenzoic acid

Product 1

HCID 41798255-Chloro-2-((2-chloroacetyl)amino)benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.0 g (17.5 mmol) of 2-amino-5-chlorobenzoic acid and 3.95 g (35.0 mmol) of chloroacetyl chloride were heated under reflux in 60 mL of toluene for 1 hour. Thereafter, the solvent was distilled off under reduced pressure, and H2O was added to the resulting residue. Solids were collected by filtration to give 4.15 g of 5-chloro-2-[(chloroacetyl)amino]benzoic acid (yield: 96%).

Workup

  1. distillationThereafter, the solvent was distilled off under reduced pressure, and H2O
  2. additionwas added to the resulting residue
  3. filtrationSolids were collected by filtration

Sources & evidence

ORD record
ord-bf9d4edb664044ad9b7d31130bcf1dd9
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Linked notes

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