Hydrochloric Acid → 3-methyl-N-(phenylthioacetyl)anthranilic acid

HRID 1587423Notes

Reaction equation

HRID 1587423 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[C:12]1([CH2:18][C:19](Cl)=[S:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>[OH-].[Na+]>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH:11][C:19](=[S:20])[CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 781012-Amino-3-methylbenzoic acidHCID 19906501Benzylthiocarbonyl chloride

Product 1

HCID 197577653-methyl-N-(phenylthioacetyl)anthranilic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Benzenethiol and butyl bromoacetate were reacted by a conventional method and then hydrolyzed to obtain α-phenylthioacetatic acid. α-phenylthioacetatic acid was reacted with thionyl chloride by a convention method to obtain α-phenylthioacetyl chloride. 3-Methylanthranilic acid 5g (33 mmol) was dissolved in 10% aqueous sodium hydroxide solution 27 ml and to this solution, α-phenylthioacetyl chloride 5.5 ml (33 mmol) was added dropwise at 0° C. The resulting solution was stirred at room temperature for 1 hour and neutralized with 10% hydrochloric acid solution. Deposited crystals were collected by filtration and recrystallized from ethanol and water to obtain 3-methyl-N-(phenylthioacetyl)anthranilic acid (melting point: 148° to 150° C.) 8.8 g (yield: 89%).

Workup

  1. additionwas added dropwise at 0° C
  2. filtrationDeposited crystals were collected by filtration
  3. customrecrystallized from ethanol and water

Sources & evidence

ORD record
ord-d8090f90e2164fe280913bf7f276859d
Source dataset
uspto-grants-1993_06
Patent number
US05217961

Reaction notes

Loading…