Aspirin → HCID 10519929, compound

Acetylsalicyclic acid (10 g, 55 mmol) was added to thionyl chloride (8.1 ml, 110 mmol) and the suspension refluxed to complete dissolution of the acid. The yellow solution was then cooled at room temperature and thionyl chloride evaporated under reduced pressure. Crude acyl chloride was dissolved in chloroform and the solvent removed under reduced pressure to give a reddish oil. This procedure was repeated three times. The oil was dissolved in dichloromethane (100 ml) and the resulting solution slowly added at 0° C. to a solution of 4-trifluoromethylaniline (6.3 ml, 50 mmol) and triethylamine (23 ml, 166 mmol) in dichloromethane (100 ml). The mixture was stirred overnight at room temperature then the organic solution was washed successively with 1N HCl (2×200 ml), 1N NaOH (200 ml) and water (200 ml). The organic phase was dried with anhydrous sodium sulphate and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel (eluent n-hexane-ethyl acetate 8:2) giving 13 g (80%) of pure N-(4-trifluoromethylphenyl)-2-acetoxy-benzamide as a white solid.

1. temperaturethe suspension refluxed
2. dissolutiondissolution of the acid
3. customthionyl chloride evaporated under reduced pressure
4. dissolutionCrude acyl chloride was dissolved in chloroform
5. customthe solvent removed under reduced pressure
6. customto give a reddish oil
7. washthe organic solution was washed successively with 1N HCl (2×200 ml), 1N NaOH (200 ml) and water (200 ml)
8. dry with materialThe organic phase was dried with anhydrous sodium sulphate
9. customevaporated under reduced pressure
10. customThe crude product was purified by flash chromatography on silica gel (eluent n-hexane-ethyl acetate 8:2)

ORD record

ord-e3200b29d9644b6491c72bba388cc684

Source dataset

uspto-grants-1999_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05905090