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

HRID 1446876노트

반응식

HRID 1446876 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-10b0c5d639b749809c0ac19467ed0a9f
출처 데이터셋
uspto-grants-1982_02
특허 번호
US04314065

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