Sodium 1-oxidopyridin-1-ium-2-thiolate → 2-[1-(2,6-Difluorophenyl)ethylthio]pyridine 1-oxide

HRID 1903832

Reaktionsgleichung

Reaktionsgleichung von HRID 1903832
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[CH:4](Cl)[CH3:5].[CH:12]1[CH:13]=[CH:14][N+:15]([O-:19])=[C:16]([S-:18])[CH:17]=1.[Na+]>C(O)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[CH:4]([S:18][C:16]1[CH:17]=[CH:12][CH:13]=[CH:14][N+:15]=1[O-:19])[CH3:5]

Komponenten

4

Edukt 2

HCID 1569Sodium 1-oxidopyridin-1-ium-2-thiolateHCID 5880552-(1-Chloroethyl)-1,3-difluorobenzene

Produkt 1

HCID 133042812-[1-(2,6-Difluorophenyl)ethylthio]pyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

2,6-Difluoro-alpha-methylbenzyl chloride (16.6 g, 0.094 mol) is dissolved in ethanol (40 ml) and warmed to 75° C. A 40 percent solution of sodium omadine (38.5 g, 0.103 mol) is added dropwise over a period of 30 minutes maintaining a reaction temperature of 75° C. throughout. Once the addition is complete, the reaction mixture is kept between 75° C. and 80° C. for 2 hours. Thereafter the mixture is quenched in ice-water and crude product is filtered off. After recrystallization with ethyl acetate pure title product (10.65 g, 42.4%) is obtained; Melting Point 158°-160° C.

Aufarbeitung

  1. temperaturemaintaining a reaction temperature of 75° C. throughout
  2. additionOnce the addition
  3. customThereafter the mixture is quenched in ice-water
  4. filtrationcrude product is filtered off
  5. customAfter recrystallization with ethyl acetate pure title product (10.65 g, 42.4%)
  6. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-f4934dcd00384e88ac9ff6de521ca032
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04438271

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