Anthranilic Acid → HCID 19974595, compound

HRID 1451640Notes

Reaction equation

HRID 1451640 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13]([OH:22])(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH2:16].C(=O)([O-])[O-].[K+].[K+].O>COCCOCCO.[Cu]>[C:13]([C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acid

Product 1

HCID 19974595HCID 19974595, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

A mixture of 2-chloro-5-(methylthio)benzoic acid (10 g), anthranilic acid (7 g), potassium carbonate (14 g) and copper (1 g) in 2-(2-methoxyethoxy)ethanol (100 ml) was heated at 180° for 24 h. Water (400 ml) was then added, and the catalyst was filtered off. The filtrate was acidified with dilute hydrochloric acid. The resulting precipitate was filtered off, washed with water, dried, and crystallised from methanol to give the title compound (4.5 g) as crystals. IR includes peaks at 3300 cm-1 (NH) and 1700 cm-1 (CO2H).

Workup

  1. temperaturewas heated at 180° for 24 h
  2. filtrationthe catalyst was filtered off
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customcrystallised from methanol

Sources & evidence

ORD record
ord-e5607978b25d4d04a49c679fdfc77762
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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