Anthranilic Acid → HCID 19757766, compound

HRID 1587424Notes

Reaction equation

HRID 1587424 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19](Cl)=[S:20])[CH:15]=[CH:16][CH:17]=1.Cl.CCOCC>[OH-].[Na+]>[CH3:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([NH:4][C:3]2[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([OH:10])=[O:9])=[S:20])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 18547076HCID 18547076, compound

Product 1

HCID 19757766HCID 19757766, compoundYield 957.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-Methylbenzenethiol and butyl bromoacetate were reacted by a conventional method and then hydrolyzed to obtain 3-methyl-α-phenylthioacetatic acid. 3-Methyl-α-phenylthioacetatic acid was reacted with thionyl chloride by a conventional method to obtain 3-methyl-α-phenylthioacetyl chloride. Anthranilic acid 5.6 g (4.1 mmol) was dissolved in 10% aqueous sodium hydroxide solution 32 ml and to this solution, 3-methyl-α-phenylthioacetyl chloride (99° C./3.3 mmHg) 8.9 g was added dropwise at 0° C. The resulting solution was stirred at room temperature for 20 minutes and neutralized with 10% hydrochloric acid solution. To this solution, ether was added, and deposited crystals were collected by filtration and washed with hot water to obtain N-(3-methylphenylthioacetyl)anthranilic acid (melting point: 148° to 150° C.) 11.2 g (yield: 25%).

Workup

  1. additionwas added dropwise at 0° C
  2. filtrationwere collected by filtration
  3. washwashed with hot water

Sources & evidence

ORD record
ord-8811d0e39015425499e95752035af04e
Source dataset
uspto-grants-1993_06
Patent number
US05217961

Reaction notes

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