Thiophosgene → 3-Isothiocyanato-4-methoxypyridine

HRID 333589

Reaktionsgleichung

Reaktionsgleichung von HRID 333589
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([O-])(O)=O.[Na+].[C:15](Cl)(Cl)=[S:16]>C(Cl)(Cl)Cl.O>[N:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9])=[C:15]=[S:16]

Komponenten

6

Edukt 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 52003433-Amino-4-methoxypyridine

Produkt 1

HCID 866653953-Isothiocyanato-4-methoxypyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred mixture of 3-amino-4-methoxypyridine (2.01 g, 16.2 mmol) and NaHCO3 (4.08 g, 48.6 mmol) in CHCl3 and water (1:1, 50 mL) at 4° C. was added thiophosgene (1.5 mL, 19.6 mmol) dropwise. After completion of the addition, the ice bath was removed. The mixture was stirred for 4 hours, the organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic phases were washed with water, dried over Na2SO4, filtered, and concentrated to give the title compound as brown solid.

Aufarbeitung

  1. additionAfter completion of the addition
  2. customthe ice bath was removed
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db54b7916c324950a910de618568492c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883473B2

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