Triethylamine → HCID 68552046, compound

Temperature

5 °C

4-Bromo-2-nitrobenzoic acid (30.0 g, 118.3 mmol) was placed in 300 mL dichloromethane and 16.5 mL triethylamine was added. Then the reaction solution heated up and a change in color from yellow to greenish brown was observed. The mixture was then cooled to 5° C. and isobutyl chloroformate (16 mL, 118.3 mmol) was added by drops without dilution. The reaction mixture was allowed to come to room temperature while stirring and stirring was continued for 1.5 hours. The mixture was cooled again to 5° C. and 2,6-dimethoxybenzylamine (19.8 g, 118.3 mmol) was added by portions. Again 300 mL dichloromethane was added for dilution and stirring was continued for 15 minutes at 5° C. and then for 12 hours at room temperature. The clear reaction mixture ultimately changed color from red to brown and the reaction was monitored by thin-layer chromatography. The batch was extracted with water, the separated organic phase was extracted with 5% citric acid (2×), washed with sodium bicarbonate solution until neutral (1×) and extracted with saturated sodium chloride solution. The organic phase was dried over sodium sulfate, the solvent was removed in vacuo. The residue was dissolved in diethyl ether/pentane solvent and the precipitate which gradually formed therefore was ultimately filtered out. Crystalline 4-bromo-N-(2,6-dimethoxybenzyl)-2-nitrobenzamide was isolated. Yield: 35.4 g (89.6 mmol, 76%).

1. temperatureThen the reaction solution heated up
2. customto come to room temperature
3. stirringstirring
4. temperatureThe mixture was cooled again to 5° C.
5. stirringstirring
6. waitwas continued for 15 minutes at 5° C.
7. waitfor 12 hours at room temperature
8. extractionThe batch was extracted with water
9. extractionthe separated organic phase was extracted with 5% citric acid (2×)
10. washwashed with sodium bicarbonate solution until neutral (1×)
11. extractionextracted with saturated sodium chloride solution
12. dry with materialThe organic phase was dried over sodium sulfate
13. customthe solvent was removed in vacuo
14. dissolutionThe residue was dissolved in diethyl ether/pentane solvent
15. customthe precipitate which gradually formed
16. filtrationtherefore was ultimately filtered out

ORD record

ord-936c5a839aaa438bac6079c2f3e8bae9

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686002B2