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

HRID 382897

反応式

HRID 382897 の反応式
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>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:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

参加物

5

反応物 3

HCID 227Anthranilic AcidHCID 73974-Toluenesulfonyl chloride2 回HCID 10340Sodium Carbonate

生成物 1

HCID 22763Benzoic acid, 2-(((4-methylphenyl)sulfonyl)amino)-収率 78.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
78 °C

実験手順

In a 1 L reaction flask equipped with a condenser, 34.25 g (0.25 mol) of anthranilic acid, 411 g of water and 63.59 g (0.6 mol) of sodium carbonate were heated. The resulting reaction solution was maintained at an inner temperature of 78° C. for 30 minutes and then cooled to 67° C., and 57.2 g (0.3 mol) of tosyl chloride was added in two portions. The reaction solution gradually generated heat upon addition of tosyl chloride and turned homogeneous at 78° C. The reaction solution was aged at 80° C. for 1 hour. Crystals started to separate out in the first ten or so minutes of the aging. The completion of the reaction was confirmed by liquid chromatography, and the reaction solution was carefully neutralized with concentrated hydrochloric acid and allowed to cool. The crystals were collected by filtration at room temperature and washed with 100 ml of dilute hydrochloric acid at pH 3 and with 125 ml of water. Recrystallization from 247 g of n-propanol afforded 56.97 g of tosylanthranilic acid in a 78.3% yield.

後処理

  1. customIn a 1 L reaction flask
  2. customequipped with a condenser
  3. customThe resulting reaction solution
  4. temperaturecooled to 67° C.
  5. customturned homogeneous at 78° C
  6. customto separate out in the first ten or so minutes of the aging
  7. temperatureto cool
  8. filtrationThe crystals were collected by filtration at room temperature
  9. washwashed with 100 ml of dilute hydrochloric acid at pH 3 and with 125 ml of water
  10. customRecrystallization from 247 g of n-propanol

出典と根拠

ORDレコード
ord-72988cf95c4c414bb1dfbac05dffe9d8
出典データセット
uspto-grants-2001_10
特許番号
US06310249B1

関連ノート

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