Hydrochloric Acid → 2-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxy-2-methylpropanoic acid

HRID 1651159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651159
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:3]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[K+].Cl>CN(C)C(=O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([O:10][S:20]([CH3:19])(=[O:22])=[O:21])=[O:9])[N:3]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 516893Potassium BicarbonateHCID 15077653(Z)-2-((((5-Amino-1,2,4-thiadiazol-3-yl)(carboxy)methylene)amino)oxy)-2-methylpropanoic acid

Produkt 1

HCID 879472882-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxy-2-methylpropanoic acidAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetic acid (2.74 g) in N,N-dimethylacetamide (45 ml) were added methanesulfonyl chloride (1.15 g) and potassium bicarbonate (1.20 g) under cooling in an ice bath. The mixture was stirred for 2.5 hours at 5° C. and poured into a cold mixture of water (200 ml), ethyl acetate (200 ml) and 1N hydrochloric acid (6 ml). The mixture was stirred for 5 minutes under cooling in an ice bath. The organic layer was separated, washed with cold water (200mlx2) and with a cold saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. Toluene was added to the residue. To the mixture was added methylene chloride and the mixture was cooled for 10 minutes in an ice bath. The crystals were collected by filtration, washed with methylene chloride and air-dried to give methanesulfonyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetate (1.1 g).

Aufarbeitung

  1. temperatureunder cooling in an ice bath
  2. stirringThe mixture was stirred for 5 minutes
  3. temperatureunder cooling in an ice bath
  4. customThe organic layer was separated
  5. washwashed with cold water (200mlx2) and with a cold saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionToluene was added to the residue
  9. additionTo the mixture was added methylene chloride
  10. temperaturethe mixture was cooled for 10 minutes in an ice bath
  11. filtrationThe crystals were collected by filtration
  12. washwashed with methylene chloride
  13. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-14e015c9e82c435c89897b00aab15bf5
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927818

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