Sodium Bicarbonate → 2-(2-Formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acid

HRID 894765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894765
P(O)(O)(O)=O.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([CH2:11][O:12][NH2:13])=[CH:9][C:8]=1[OH:16].C(=O)(O)[O-].[Na+].[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=O)[C:31]([OH:33])=[O:32])[N:29]=1)=[O:23]>O.C(O)C>[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:13][O:12][CH2:11][C:10]2[CH:14]=[CH:15][C:7]([Br:6])=[C:8]([OH:16])[CH:9]=2)[C:31]([OH:33])=[O:32])[N:29]=1)=[O:23]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 236167634-Bromo-3-hydroxybenzyloxyamine phosphate

Produkt 1

HCID 540633902-(2-Formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acidAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The solution of 4-bromo-3-hydroxybenzyloxyamine phosphate (17.4 g.) in water (200 ml.) and ethanol (200 ml.) was stirred at room temperature and adjusted to pH 7.0 with sodium bicarbonate. 2-(2-Formamidothiazol-4-yl)glyoxylic acid (10.0 g.) was added to the solution and the resulting suspension was adjusted to pH 4.0 to 4.5. After stirring the solution at room temperature for 2 hours, ethanol was removed from the resultant solution in vacuo. Ethyl acetate was added to aqueous residue and adjusted to pH 2.5 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with water and dried over magnesium sulfate. The solution was concentrated in vacuo to give 2-(2-formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acid (syn isomer, 14.8 g.).

Aufarbeitung

  1. customethanol was removed from the resultant solution in vacuo
  2. additionEthyl acetate was added to aqueous residue
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f4d9392e31ac4309adeb0a71038da935
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284631

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