Hydrochloric Acid → HCID 66817245, compound

Temperature

0 °C

p-Nitrophenyl chloroformate (437 mg, 2.17 mmol) was added to a solution of 4-bromo-3-trifluoromethyl-aniline (400 μl, 1.67 mmol) and pyridine (202 μl, 2.50 mmol) in CH2Cl2 (6.2 ml) at 0° C. The mixture was stirred at 0° C. for one hour, and 2-amino-ethanol (150 μl, 2.50 mmol) was then added, followed by further stirring at 0° C. for two hours. Triethylamine (210 μl, 1.51 mmol) was added to the mixture, and the mixture was stirred at 0° C. for one hour. 1 N HCl was added to the reaction mixture, followed by extraction with CH2Cl2/AcOEt. The organic layer was washed with water (×2), and then dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2-MeOH) to give 1-(4-bromo-3-trifluoromethyl-phenyl)-3-(2-hydroxy-ethyl)-urea as a white powder (520 mg, 73%).

1. stirringby further stirring at 0° C. for two hours
2. stirringthe mixture was stirred at 0° C. for one hour
3. extractionfollowed by extraction with CH2Cl2/AcOEt
4. washThe organic layer was washed with water (×2)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (CH2Cl2-MeOH)

ORD record

ord-1549bcb9e4ad441a919d2f1adebf17cf

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2