Anthranilic Acid → N-(2-carboxyphenyl)glycine

HRID 1162163ノート

反応式

HRID 1162163 の反応式
Cl[CH2:2][C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[C:12]([OH:21])(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:15]>O.[OH-].[Na+]>[C:3]([CH2:2][NH:15][C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1[C:12]([OH:21])=[O:20])([OH:5])=[O:4]

参加物

6

反応物 3

HCID 227Anthranilic AcidHCID 300Chloroacetic AcidHCID 10340Sodium Carbonate

生成物 1

HCID 69161N-(2-carboxyphenyl)glycine

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 14798Sodium Hydroxide溶媒2 回

反応条件

温度
42.5 °C

実験手順

To a solution of chloroacetic acid (347 g, 3.67 mol) in water (500 mL), sodium carbonate (200 g, 4.72 mol) was carefully added at room temperature under stirring. The formed solution was heated to 40-45° C. and quickly added to a mixture prepared from a suspension of anthranilic acid (500 g, 3.65 mol) in water (340 mL) and 35% aqueous sodium hydroxide solution (320 mL) and heated to 40-45° C. The reaction mixture was kept at 40° C. for 4 days and the solid reaction mixture was treated with a solution of sodium hydroxide (150 g, 3.75 mol) in water (4 L). The mixture was heated to 60° C. and filtered off while hot. The solid residue was washed on the filter with 20% aqueous sodium hydroxide until the solid residue was dissolved, and the combined filtrates were acidified with 37% aqueous hydrochloric acid to pH 3. The precipitate was filtered off; an additional amount of the product precipitated overnight from the filtrate and was collected. The product was dried at 100° C. to give total 567 g (80%), m.p. 220° C.

後処理

  1. additionquickly added to a mixture
  2. temperatureheated to 40-45° C
  3. customthe solid reaction mixture
  4. temperatureThe mixture was heated to 60° C.
  5. filtrationfiltered off while hot
  6. washThe solid residue was washed on the
  7. filtrationfilter with 20% aqueous sodium hydroxide until the solid residue
  8. dissolutionwas dissolved
  9. filtrationThe precipitate was filtered off
  10. customan additional amount of the product precipitated overnight from the filtrate
  11. customwas collected
  12. customThe product was dried at 100° C.
  13. customto give total 567 g (80%), m.p. 220° C.

出典と根拠

ORDレコード
ord-3fe1c94b884147f2a2377bdbdbcddab9
出典データセット
uspto-grants-2010_10
特許番号
US07820691B2

反応ノート

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