Anthranilic Acid → Benzoic acid, 2-(((4-methylphenyl)sulfonyl)amino)-

HRID 23769

Reaktionsgleichung

Reaktionsgleichung von HRID 23769
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+].Cl>O>[S:17]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Komponenten

6

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

99.26 g of anthranilic acid was added to 830 g of water, the resulting mixture was heated at 75° C. and 165.3 g of p-toluenesulfonyl chloride was added thereto over 30 minutes with stirring. 495 g of 28% aqueous solution of sodium hydroxide was added dropwise and the mixture was stirred at 80° C. for one hour. The reaction mixture was added dropwise to a mixed solution of 360 g of 35% hydrochloric acid and 270 g of water at 70 to 80° C. and stirred for one hour. After cooling to 30° C., the mixture was filtered, the resulting crystals were washed with water, and the wet crystals were heated and solved in 750 g of 1-propanol to obtain a solution. After cooling to a room temperature, the solution was filtered, the resulting crystals were washed with 1-propanol, and dried under a reduced pressure to obtain 175 g of N-tosyl anthranilic acid.

Aufarbeitung

  1. stirringthe mixture was stirred at 80° C. for one hour
  2. stirringstirred for one hour
  3. temperatureAfter cooling to 30° C.
  4. filtrationthe mixture was filtered
  5. washthe resulting crystals were washed with water
  6. temperaturethe wet crystals were heated
  7. customto obtain a solution
  8. temperatureAfter cooling to a room temperature
  9. filtrationthe solution was filtered
  10. washthe resulting crystals were washed with 1-propanol
  11. customdried under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6b42f002bf04ae1b1cd8f19a1bb7b9e
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852862B2

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