Thionyl Chloride → HCID 12233737, compound

Temperature

130 °C

A mixture of 2-amino-5-bromo-benzoic acid (2 g, 9.26 mmol) and SOCl2 (4 mL) in toluene (20 mL) was stirred at 130° C. for 2 h. After being concentrated, the residue was dissolved in tetrahydrofuran (50 mL) and phenylamine was added dropwise at 0° C. Then the reaction mixture was heated to 90° C. for 4 h. The mixture was cooled to room temperature, quenched with saturated aqueous K2CO3 (20 mL) and extracted with ethyl acetate (50 mL*3), the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel column chromatograph (PE:EtOAc=4:1) to give 2-amino-5-bromo-N-phenylbenzamide (2.82 g, yield: 99%) as white solid. MS (M+H)+: 291/293.

1. concentrationAfter being concentrated
2. dissolutionthe residue was dissolved in tetrahydrofuran (50 mL)
3. additionphenylamine was added dropwise at 0° C
4. temperatureThen the reaction mixture was heated to 90° C. for 4 h
5. temperatureThe mixture was cooled to room temperature
6. customquenched with saturated aqueous K2CO3 (20 mL)
7. extractionextracted with ethyl acetate (50 mL*3)
8. washthe combined organic layers were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified with silica gel column chromatograph (PE:EtOAc=4:1)

ORD record

ord-ad790e591e994e5f949ea023178dbacf

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09364482B2