Hydrochloric Acid → Phthalonitrile

Temperature

165 °C

In 180 ml of an N,N-dimethylacetamide/1-methyl-2-pyrrolidone (=1/1 volume ratio) mixed solvent were dissolved 30 g of 3-nitrophthalonitrile, to which 11.97 g of sodium nitrite were added. The mixture was stirred at 165° C. for 40 minutes. After being cooled to room temperature, the mixture was added with 16.8 g of potassium carbonate, which was further stirred at 150° C. for 40 minutes and thereafter cooled to 40° C. Then, 25 g of chloromethyltrimethylsilane were added dropwise. After the addition, the mixture was stirred for 28 hours while maintaining the reaction temperature at 80°-90° C. The reaction vessel was then cooled to room temperature and 350 ml of dilute hydrochloric acid was added. The mixture was extracted with 1.5 liters of toluene. The organic layer was washed well with water and water was removed with magnesium sulfate. Thereafter, toluene was removed by distillation and the residue was purified with a toluene/silica gel column to obtain 29.8 g (yield: 74.7%) of a compound having the above-described formula (XV).

1. temperatureAfter being cooled to room temperature
2. stirringwas further stirred at 150° C. for 40 minutes
3. temperaturecooled to 40° C
4. additionAfter the addition
5. stirringthe mixture was stirred for 28 hours
6. temperaturewhile maintaining the reaction temperature at 80°-90° C
7. temperatureThe reaction vessel was then cooled to room temperature
8. extractionThe mixture was extracted with 1.5 liters of toluene
9. washThe organic layer was washed well with water and water
10. customwas removed with magnesium sulfate
11. customThereafter, toluene was removed by distillation
12. customthe residue was purified with a toluene/silica gel column

ORD record

ord-ead03d4903234b6a860ceaeb23f2100b

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05677025