Anthranilic Acid → 2-(4-Methyl-1,2,3-thiadiazol-5-yl-carbonylamino)benzoic acid

HRID 1699652Notes

Reaction equation

HRID 1699652 reaction equation
[OH-].[Na+].[C:3]([OH:12])(=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH2:6].[CH3:13][C:14]1[N:15]=[N:16][S:17][C:18]=1[C:19](Cl)=[O:20]>O>[CH3:13][C:14]1[N:15]=[N:16][S:17][C:18]=1[C:19]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[C:3]([OH:12])=[O:11])=[O:20]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 14798Sodium HydroxideHCID 27369824-Methyl-1,2,3-thiadiazole-5-carbonyl chloride

Product 1

HCID 75767242-(4-Methyl-1,2,3-thiadiazol-5-yl-carbonylamino)benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 50 ml of water were dissolved 1.2 g (31 mmol) of sodium hydroxide and 4.2 g (31 mmol) of anthranilic acid. While cooling the solution with ice, 5 g (31 mmol) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid chloride was dropwise added thereto over a period of 30 minutes. After the dropping, the resulting mixture was reacted with stirring at room temperature for 30 minutes. After the reaction was completed, the crystalline product deposited from the reaction mixture was collected by filtration and washed with methanol and ethyl acetate. Thus, 7.1 g of the objective compound was obtained.

Workup

  1. additionwas dropwise added
  2. customAfter the dropping, the resulting mixture was reacted
  3. filtrationwas collected by filtration
  4. washwashed with methanol and ethyl acetate

Sources & evidence

ORD record
ord-776629999dc340f68ff3896e45ad5ee3
Source dataset
uspto-grants-2002_02
Patent number
US06348460B1

Reaction notes

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