Tetrachlorophthalic anhydride → 2,3,4,5-Tetrachloro-6-[(4-chloro-3-isopropoxycarbonyl-phenyl)carbamoyl]benzoic acid

HRID 326343

Reaction equation

HRID 326343 reaction equation
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:29])=[C:21]([CH:28]=1)[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23]>C1(C)C=CC=CC=1>[Cl:13][C:5]1[C:4]([Cl:14])=[C:3]([Cl:15])[C:2]([Cl:1])=[C:7]([C:8]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:29])=[C:21]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:28]=2)=[O:9])[C:6]=1[C:11]([OH:10])=[O:12]

Participants

4

Reactant 2

HCID 8326Tetrachlorophthalic anhydrideHCID 369590Isopropyl 5-amino-2-chlorobenzoate

Product 1

HCID 5032772,3,4,5-Tetrachloro-6-[(4-chloro-3-isopropoxycarbonyl-phenyl)carbamoyl]benzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tetrachlorophthalic anhydride (2.97 g, 0.010 mole), 1-methylethyl 5-amino-2-chlorobenzoate (2.22 g, 0.010 mole) and toluene (100 ml) was heated slowly to reflux with stirring, then left overnight at room temperature. Filtration of the reaction mixture gave the title compound, m.p. 178°-179° C. (3.45 g, 70% yield).

Workup

  1. temperaturewas heated slowly
  2. temperatureto reflux
  3. filtrationFiltration of the reaction mixture

Sources & evidence

ORD record
ord-04dd752ccf414eb685ac6e3834415e2e
Source dataset
uspto-grants-1993_12
Patent number
US05268389

Linked notes

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