1,3-Dichloro-5,5-dimethylhydantoin → Methyl 3-amino-2-chloroisonicotinate

HRID 1940917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940917
[NH2:1][C:2]1[CH:11]=[N:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:12]N1C(C)(C)C(=O)N(Cl)C1=O>ClC(Cl)=C(Cl)Cl>[NH2:1][C:2]1[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 1488824Methyl 3-aminopyridine-4-carboxylate

Produkt 1

HCID 2762510Methyl 3-amino-2-chloroisonicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31373TetrachloroethyleneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 18 g (118 mmol) of methyl 3-aminoisonicotinate and 12 g (60 mmol) of 1,3-dichloro-5,5-dimethylhydantoin in 1500 mL of tetrachloroethylene was warmed slowly to 80° C. with stirring and held there for 3 hours. The solution was then cooled, filtered, washed with dilute aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a dark oil. This oil was purified by careful column chromatography to obtain 6.7 g (30 percent of theory) of the title compound as a colorless solid melting at 91°-92° C.

Aufarbeitung

  1. temperatureThe solution was then cooled
  2. filtrationfiltered
  3. washwashed with dilute aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customto obtain a dark oil
  8. customThis oil was purified by careful column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9e1fc36cf51949b5b3343e1755530015
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700940

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