Acetone → HCID 19813123, compound

Temperature

5 °C

A mixture of 4-acetoxybenzoic acid (5.0 g) and triethylamine (3.0 g) in acetone (150 mL) at 0° C. was treated with ethyl chloroformate over 5 minutes with stirring. After a further 10 minutes, sodium azide (21.5 g) in water (10 mL) was added and the mixture maintained at 5° C. for 0.5 hour. The mixture was then concentrated at 45° C. under reduced pressure and the residue dissolved in toluene (200 mL) and washed with water and dried (Na2SO4). After evaporation of 100 mL of the toluene under reduced pressure, the solution was heated under reflux for 1 hour and cooled to 5° C. before addition of n-propylamine (3 mL). After a further 15 minutes, the mixture was evaporated to dryness and the residue dissolved in methanol (50 mL) and warmed with 10% aqueous NaOH (10 mL) at 60° C. for 15 minutes. Evaporation of the methanol and addition of water and 6N HCl gave a solid which was filtered, washed with water and crystallized from acetone-ether to give 4-n-propylaminocarbonylaminophenol (3.1 g).

1. concentrationThe mixture was then concentrated at 45° C. under reduced pressure
2. dissolutionthe residue dissolved in toluene (200 mL)
3. washwashed with water
4. dry with materialdried (Na2SO4)
5. customAfter evaporation of 100 mL of the toluene under reduced pressure
6. temperaturethe solution was heated
7. temperatureunder reflux for 1 hour
8. temperaturecooled to 5° C. before addition of n-propylamine (3 mL)
9. waitAfter a further 15 minutes
10. customthe mixture was evaporated to dryness
11. dissolutionthe residue dissolved in methanol (50 mL)
12. temperaturewarmed with 10% aqueous NaOH (10 mL) at 60° C. for 15 minutes
13. customEvaporation of the methanol and addition of water and 6N HCl
14. customgave a solid which
15. filtrationwas filtered
16. washwashed with water
17. customcrystallized from acetone-ether

ORD record

ord-3347c298cce04a49a10ef3e1edf63a9f

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05158949