Thionyl Chloride → HCID 86713980, compound

2-Chloro-4,5-dinitrobenzoic acid (known from WO-A-2009/47558) (8.0 g, 32.5 mmol) was dissolved in 1,2-dichloroethane (80 ml), and thionyl chloride (20 ml) was added under nitrogen. The reaction mixture was heated under reflux for 4 h and then the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (80 ml) and, at 0° C., cyclopropylamine (2.4 ml, 39 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and then the solvent was removed under reduced pressure. The residue was stirred with diethyl ether (50 ml) for 30 min and then filtered off with suction. The residue was washed with water (100 ml) and dried. 7.5 g (81% of theory) of 2-chloro-N-cyclopropyl-4,5-dinitrobenzamide were thus obtained.

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 4 h
3. customthe solvent was removed under reduced pressure
4. dissolutionThe residue was dissolved in dichloromethane (80 ml) and, at 0° C.
5. customthe solvent was removed under reduced pressure
6. stirringThe residue was stirred with diethyl ether (50 ml) for 30 min
7. filtrationfiltered off with suction
8. washThe residue was washed with water (100 ml)
9. customdried

ORD record

ord-99ab0aad557d46eab76a008accfd8f43

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09107411B2