Potassium Hydroxide → Methyl 3-(N,N-dimethylaminothiocarbamoyloxy)pyridine-2-carboxylate

HRID 35545

Reaktionsgleichung

Reaktionsgleichung von HRID 35545
[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH3:14][NH:15][N:16]([NH:20][CH3:21])[C:17](Cl)=[S:18]>O>[CH3:14][NH:15][N:16]([NH:20][CH3:21])[C:17]([O:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)=[S:18]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylateHCID 86742401N,N-dimethylaminothiocarbamoyl chloride

Produkt 1

HCID 86742400Methyl 3-(N,N-dimethylaminothiocarbamoyloxy)pyridine-2-carboxylateAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 3.06 g (20 mmol) of methyl 3-hydroxypyridine-2-carboxylate in 15 mL of water was made basic with 1.12 g KOH. To this solution was added 3.2 g (26 mmol) of N,N-dimethylaminothiocarbamoyl chloride and the solution was stirred at room temperature for 2 hours. The solution was partitioned between benzene and water and the aqueous layer was washed with two portions of water. The combined extracts were dried and concentrated to afford 4.1 g of a white solid, m.p. 74°-75° C.

Aufarbeitung

  1. customThe solution was partitioned between benzene and water
  2. washthe aqueous layer was washed with two portions of water
  3. customThe combined extracts were dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b9c88c351b54a55b8f8e3550258e9d6
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767766

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