Hydrochloric Acid → 2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid

HRID 28286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28286
[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)[C:5]([O:7]CC)=[O:6].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)[C:5]([OH:7])=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetateHCID 178472869HCID 178472869, Verbindung

Produkt 1

HCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Ethanol (10 ml.) was added to a suspension of ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate (syn isomer), which can be represented as ethyl 2-methoxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetate (syn isomer), (2.2 g.) in a 1 N aqueous solution of sodium hydroxide (12 ml.) and the mixture was stirred for 15 hours at ambient temperature. The reaction mixture was adjusted to pH 7.0 with 10% hydrochloric acid and ethanol was distilled off under reduced pressure. The residual aqueous solution was washed with ethyl acetate, adjusted to pH 2.8 with 10% hydrochloric acid and stirred under ice-cooling to precipitate crystals. The crystals were collected by filtration, washed with acetone and recrystallized from ethanol to give colorless needles of 2-methoxyimino-2-(2-aminothiazol-4-yl)acetic acid (syn isomer), which can be represented as 2-methoxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetic acid (syn isomer), (1.1 g.).

Aufarbeitung

  1. distillationwas distilled off under reduced pressure
  2. washThe residual aqueous solution was washed with ethyl acetate
  3. stirringstirred under ice-
  4. temperaturecooling
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed with acetone
  8. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-560b09e0caa84bf1a197f81caf390cf5
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225707

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