Nitromethane → HCID 11018972, compound

Temperature

103 °C

In a one liter glass reactor equipped with a thermometer, a cooling apparatus and a stirrer, 3-methyl-3-butenenitrile (37.0 g, 0.456 mol) and nitromethane (557.0 g, 9.125 mol) were charged. Then, 1,8-diazabicyclo[5.4.0]-7-undecene (13.9 g, 0.091 mol) was dropwise added over a period of 5 minutes at room temperature while stirring. After the dropwise addition, the mixture was heated and refluxed at 103° C. for 13.5 hours. After cooling the mixture to room temperature, unreacted nitromethane was evaporated off under reduced pressure. To the residue, dichloromethane (300 g) and 5% sulfuric acid (300 g) were added and stirred. Thereafter, the mixture was phase separated to obtain a dichloromethane layer. To the aqueous layer, dichloromethane (300 g) was added and the mixture was phase separated to obtain a dichloromethane layer. Two dichloromethane layers were combined and washed with water (300 g). After drying the dichloromethane solution over anhydrous sodium sulfate, dichloromethane was evaporated off under reduced pressure to obtain brown crystal 3,3-dimethyl-4-nitrobutanenitrile (60.7 g), a purity of which was 92.0%. Its yield was 86.1% based on 3-methyl-3-butenenitrile.

1. customIn a one liter glass reactor equipped with a thermometer
2. additionAfter the dropwise addition
3. temperaturethe mixture was heated
4. temperatureAfter cooling the mixture to room temperature
5. customunreacted nitromethane was evaporated off under reduced pressure
6. additionTo the residue, dichloromethane (300 g) and 5% sulfuric acid (300 g) were added
7. stirringstirred
8. customseparated
9. customto obtain a dichloromethane layer
10. customseparated
11. customto obtain a dichloromethane layer
12. washwashed with water (300 g)
13. dry with materialAfter drying the dichloromethane solution over anhydrous sodium sulfate, dichloromethane
14. customwas evaporated off under reduced pressure

ORD record

ord-6fcc206fab7245caa2a747761a832022

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05498725