4-(Chloromethyl)pyridinium chloride → Sodium phenyl(4-picolylthio)acetate

HRID 1389790

Reaktionsgleichung

Reaktionsgleichung von HRID 1389790
C[O-].[Na+:3].[SH:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7].C[O-].Cl.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=1>C(O)C>[C:9]1([CH:5]([S:4][CH2:24][C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)[C:6]([O-:8])=[O:7])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na+:3]

Komponenten

6

Edukt 4

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 3826051MethoxideHCID 10464709Thiomandelic acidHCID 10942334Sodium Methoxide

Produkt 1

HCID 23686690Sodium phenyl(4-picolylthio)acetateAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

Sodium methoxide (6.8 g., 0.124 mole) was dissolved in 150 ml. of ethanol and cooled to 0° C. A solution of alpha-mercaptophenylacetic acid (7.0 g., 0.042 moles) in 50 ml. of ethanol was added over a period of 5 minutes to the cold methoxide solution. After 5 minutes, a slurry of 4-picolylchloride hydrochloride (6.83 g., 0.042 moles) slurried in 50 ml. of ethanol was then added over 5 minutes. The reaction was removed from the ice bath and left to stir for approximately 60 hours. The reaction mixture was filtered and evaporated to yield sodium phenyl(4-picolylthio)acetate (11.8 g.; waxy solid; ir: 3.0, 6.1, 6.25, 7.3, 13.6μ) used directly in the next step.

Aufarbeitung

  1. customThe reaction was removed from the ice bath
  2. waitleft
  3. filtrationThe reaction mixture was filtered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6d0ca8b9148a405f9e858be20b9f9240
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04246263

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