Pyridine → Methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate

To a solution of 5.43 g of 4-nitrophenyl chloroformate in 100 mL of dichloromethane was added 2.4 mL of pyridine under ice-cooling, and 5 g of methyl 4-amino-3-chlorobenzoate was added to the obtained mixture, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue, followed by washing with 1 M hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution, water, and a saturated aqueous sodium chloride solution in this order. The organic layer was dried over anhydrous sodium sulfate, and after filtration, the filtrate was concentrated under reduced pressure. The obtained solid was dissolved in 200 mL of toluene under heating, and left to be cooled to room temperature, and further cooled in an ice bath. The precipitated solid was collected by filtration, and dried under reduced pressure to obtain 5.59 g of methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate as a white solid.

1. temperaturecooling
2. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
3. additionwas added to the residue
4. washby washing with 1 M hydrochloric acid, water
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. filtrationafter filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. dissolutionThe obtained solid was dissolved in 200 mL of toluene
9. temperatureunder heating
10. waitleft
11. temperatureto be cooled to room temperature
12. temperaturefurther cooled in an ice bath
13. filtrationThe precipitated solid was collected by filtration
14. customdried under reduced pressure

ORDレコード

ord-6a46a0be34bb463eb4e4a66bd4d312c9

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08153658B2