Sodium Chloride → HCID 20437378, compound

A solution of 40.4 g of p-nitrobenzenesulfonamide in 250 ml. of dry dimethylacetamide is added dropwise, over 30 minutes, to a stirred and cooled (water bath) suspension of 5.5 g. of sodium hydride in 100 ml. of dry dimethylacetamide. The resulting dark solution is stirred for a further 30 minutes at room temperature. In the meantime, a mixture of 36.2 g. of p-hexadecylaminobenzoic acid in 1200 ml. of methylene chloride, 300 ml. of dimethoxyethane, and 40 ml. of thionyl chloride is refluxed for 1 hour and 15 minutes. The solution is evaporated to an oil which is co-evaporated twice with added dioxane to remove excess thionyl chloride. The resulting amber oil is dissolved in 75 ml. of dry dimethylacetamide and the solution is added, over approximately 3 minutes, to the previously prepared solution of sodium p-nitrobenzenesulfonamide and cooled in an ice bath. After the addition, the ice bath is removed and the solution is stirred at room temperature for one hour. The solution is filtered through a bed of diatomaceous earth and the filtrate is poured into 2.1 of water to give a suspension. Saturated sodium chloride solution (250 ml.) followed by sodium chloride crystals (100 g.) is added to produce a finely divided precipitate. The mixture is filtered through a bed of diatomaceous earth. The product is washed with water and partially dried on the filter to give a yellow paste. The paste is dissolved in a mixture of 250 ml. of methylene chloride, 250 ml. of ethyl acetate, and 250 ml. of acetone. The solution is filtered through a bed of diatomaceous earth, a small aqueous layer separated, and the organic phase dried over anhydrous sodium sulfate. The solution is filtered and the filtrate is evaporated to an amber glass which is crystallized from 150 ml. of 1:1 ether:hexane. The product was recrystallized three times from absolute ethanol to provide 14.75 g. of the title compound as bright yellow crystals, melting point 129.5°-131° C.

1. temperaturecooled
2. stirringThe resulting dark solution is stirred for a further 30 minutes at room temperature
3. additionIn the meantime, a mixture of 36.2 g
4. customThe solution is evaporated to an oil which
5. customto remove excess thionyl chloride
6. dissolutionThe resulting amber oil is dissolved in 75 ml
7. additionof dry dimethylacetamide and the solution is added, over approximately 3 minutes, to the previously prepared solution of sodium p-nitrobenzenesulfonamide
8. temperaturecooled in an ice bath
9. additionAfter the addition
10. customthe ice bath is removed
11. stirringthe solution is stirred at room temperature for one hour
12. filtrationThe solution is filtered through a bed of diatomaceous earth
13. additionthe filtrate is poured into 2.1 of water
14. customto give a suspension
15. additionis added
16. customto produce a finely divided precipitate
17. filtrationThe mixture is filtered through a bed of diatomaceous earth
18. washThe product is washed with water
19. custompartially dried on the
20. filtrationfilter
21. customto give a yellow paste
22. dissolutionThe paste is dissolved in a mixture of 250 ml
23. filtrationThe solution is filtered through a bed of diatomaceous earth
24. customa small aqueous layer separated
25. dry with materialthe organic phase dried over anhydrous sodium sulfate
26. filtrationThe solution is filtered
27. customthe filtrate is evaporated to an amber glass which
28. customis crystallized from 150 ml
29. customThe product was recrystallized three times from absolute ethanol
30. customto provide 14.75 g

ORD record

ord-49dbcb86a707416abad7c15946f2f9da

Source dataset

uspto-grants-1984_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04485105