Sodium Hydroxide → 2-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionic acid

HRID 1446876ノート

反応式

HRID 1446876 の反応式
[CH3:1][N:2]([C:13]1[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1.[OH-].[Na+]>C(O)(C)C.O>[CH3:1][N:2]([C:13]1[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 13314823Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate

生成物 1

HCID 133148242-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionic acid収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒2 回

実験手順

Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate (10.0 g; see Example 7) was suspended in isopropyl alcohol (50 ml) and a solution of sodium hydroxide (1.12 g) in water (50 ml) was added over a period of 45 minutes. Further isopropyl alcohol (60 ml) was added and the mixture was stirred at room temperature for a period of 48 hours. The alcohol was removed by distillation under reduced pressure, the residue was dissolved in water and the aqueous solution was acidified to pH 4 by the addition of aqueous 2 M hydrochloric acid. The precipitate was collected by filtration, dried and recrystallised from ethyl acetate to give the title compound (5.83 g; 63%), mp 152°-154° C. The pmr spectrum of the compound was consistent with the assigned structure.

後処理

  1. customThe alcohol was removed by distillation under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. additionthe aqueous solution was acidified to pH 4 by the addition of aqueous 2 M hydrochloric acid
  4. filtrationThe precipitate was collected by filtration
  5. customdried
  6. customrecrystallised from ethyl acetate

出典と根拠

ORDレコード
ord-10b0c5d639b749809c0ac19467ed0a9f
出典データセット
uspto-grants-1982_02
特許番号
US04314065

反応ノート

読み込み中…