Water → 3-Pyridinecarboxylic acid, 2-[(phenylmethyl)thio]-

HRID 20250

Reaktionsgleichung

Reaktionsgleichung von HRID 20250
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH2:17]([SH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CS(C)=O>[C:18]1([CH2:17][S:24][C:8]2[C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=[CH:15][N:16]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acid

Produkt 1

HCID 7577793-Pyridinecarboxylic acid, 2-[(phenylmethyl)thio]-Ausbeute 49,07 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

In a stirred suspension of 96.37 gm potassium carbonate in 700 gm dimethyl sulphoxide, 100 gm 2-chloro nicotinic acid was charged. A solution of 82.38 gm benzyl mercaptan in 300 gm dimethyl sulphoxide was added in a period of two hours maintaining reaction temperature 80-90 deg. c. The temperature of the reaction was raised up to 140 deg. c. and then maintained for another three hours. 500 gm water was added after completion of the reaction and solvent recovery. Product precipitation achieved by lowering the pH of the reaction mass by using dilute HCl. Product 2-(Phenyl methyl thio)-3-pyridine carboxylic acid precipitated completely till pH 4.5. After filtration and washing, cake was dried to get 75.5 gm white to off white solid product 2-(Phenyl methyl thio)-3-pyridine carboxylic acid with 49.07% yield (Assay by HPLC 99.16%).

Aufarbeitung

  1. additionwas charged
  2. temperaturemaintaining
  3. customreaction temperature 80-90 deg. c
  4. temperatureThe temperature of the reaction was raised up to 140 deg. c
  5. temperatureand then maintained for another three hours
  6. customafter completion of the reaction and solvent recovery
  7. customProduct precipitation
  8. customProduct 2-(Phenyl methyl thio)-3-pyridine carboxylic acid precipitated completely till pH 4.5
  9. filtrationAfter filtration
  10. washwashing
  11. customcake was dried

Quellen und Nachweise

ORD-Eintrag
ord-0cb1c1d3ae5346018237b46c134033e7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745631B2

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