Water → 6-Isothiocyanato-2,4-dimethylnicotinonitrile

Temperatur

0 °C

A suspension of 6-amino-3-cyano-2,4-dimethylpyridine (0.1 g, 0.68 mmol) in CH2Cl2 (1 mL) was added to a vigorously stirred mixture of CaCO3 (0.41 g, 4.11 mmol) in a 1:2 water:CH2Cl2 mixture (9 mL total) at room temp. The reaction mixture was cooled to 0° C. and thiophosgene (0.09 g, 0.78 mmol) was added dropwise. The resulting mixture was allowed to warm to room temp and was stirred overnight. The resulting aqueous layer was back-extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with water (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 10% EtOAc/hex) to give 2,4-dimethyl-3-cyano-6-pyridyl isothiocyanate (0.12 g, 91%): CI-MS m/z 190 ((M+H)+).

1. customat room temp
2. temperatureto warm to room temp
3. extractionThe resulting aqueous layer was back-extracted with CH2Cl2 (3×10 mL)
4. washThe combined organic layers were washed with water (10 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography (SiO2, 10% EtOAc/hex)

ORD-Eintrag

ord-2e90a8d951224d7f91b9854854bc5ed9

Quelldatensatz

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06353006B1