Dimethylamine → HCID 178484500, compound

Temperature

0 °C

A solution of 4-nitro-1H-pyrazole-3-carboxylic acid (1.0 g, 6.4 mmol) in dichloromethane (20 ml) was treated with thionyl chloride (1.4 ml, 19 mmol) and a drop of DMF at ambient temperature. The reaction mixture is stirred at 40° C. overnight whereupon another equivalent of thionyl chloride (0.46 ml, 6.4 mmol) was added and stirring was continued at 40° C. for another 24 h. All volatiles were removed and the acid chloride was suspended in dichloromethane (6 ml) and cooled to 0° C. Triethylamine (4.44 ml, 31.8 mmol) and dimethylamin (4.14 ml, 2M solution in THF) were added. The reaction mixture was allowed to warm-up to ambient temperature and stirring was continued for 3 h. The reaction mixture was partitioned between potassium hydrogen sulfate (20 ml, 10% aqueous solution) and ethyl acetate (40 ml) and extracted. The organic phase was washed with water and brine, dried and the solvent was evaporated. The crude product was triturated with diethylether, sucked off and dried to yield a light brown solid (0.35 g, 30%).

1. customat ambient temperature
2. additionwas added
3. customAll volatiles were removed
4. temperatureto warm-up to ambient temperature
5. stirringstirring
6. waitwas continued for 3 h
7. customThe reaction mixture was partitioned between potassium hydrogen sulfate (20 ml, 10% aqueous solution) and ethyl acetate (40 ml)
8. extractionextracted
9. washThe organic phase was washed with water and brine
10. customdried
11. customthe solvent was evaporated
12. customThe crude product was triturated with diethylether
13. customdried

ORD record

ord-2f31dc2309e14f6aa59d53c8f3f3e13c

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623866B2