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

HRID 1446876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446876
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-10b0c5d639b749809c0ac19467ed0a9f
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04314065

Notizen zur Reaktion

Wird geladen…