Dimethylformamide → HCID 13257751, compound

A drop of dimethylformamide and oxalyl chloride (1 ml) were added to a solution of 2-naphthylacetic acid (840 mg, 4.5 mmol) in methylene chloride (15 ml) at room temperature. This mixture was stirred at room temperature for 30 minutes. The solvent was removed and the residue was dissolved in acetone (15 ml) and cooled to 0° C. A solution of sodium azide (700 mg, 11 mmol) in water (10 ml) was added. The reaction mixture was stirred for 30 minutes at 5° C. and was then poured into a mixture of ice water (30 ml), ether (40 ml), and hexane (40 ml). The organic phase was separated, washed with brine, dried and concentrated to 5 ml. Chloroform (5 ml) was added to the residue. The resultant solution was added to chloroform (10 ml) at 80° C. dropwise. The mixture was heated at reflux for 1 hour. The solvent was evaporated to give 680 mg of crude product. Purification by chromatography (silica, methylene chloride) gave 342 mg of the desired product as a white solid. IR (neat) 2355 cm−1, 2336 cm−1, 2267 cm−1.

1. customThe solvent was removed
2. dissolutionthe residue was dissolved in acetone (15 ml)
3. temperaturecooled to 0° C
4. stirringThe reaction mixture was stirred for 30 minutes at 5° C.
5. customThe organic phase was separated
6. washwashed with brine
7. customdried
8. concentrationconcentrated to 5 ml
9. additionChloroform (5 ml) was added to the residue
10. additionThe resultant solution was added to chloroform (10 ml) at 80° C. dropwise
11. temperatureThe mixture was heated
12. temperatureat reflux for 1 hour
13. customThe solvent was evaporated
14. customto give 680 mg of crude product
15. customPurification by chromatography (silica, methylene chloride)

ORD record

ord-257b5bcb1c874308bbbc295fd6c4ed9f

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06335324B1