Benzenesulfonamide → HCID 53681197, compound

HRID 325564Notes

Reaction equation

HRID 325564 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:13]([NH:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](O)=[O:32])[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].S(Cl)(Cl)=O>C(COC)OC.C(Cl)Cl.CC(N(C)C)=O>[CH2:13]([NH:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([NH:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])=[O:32])[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 7370BenzenesulfonamideHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 53989503HCID 53989503, compound

Product 1

HCID 53681197HCID 53681197, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 31.4 g. of benzenesulfonamide in 250 ml. of dry dimethylacetamide is added dropwise, with stirring and cooling, to a suspension of 5.5 g. of sodium hydride in 100 ml. of dry dimethylacetamide over 30 minutes at room temperature. Stirring is continued for a further 30 minutes. In the meantime, a mixture of 36.2 g. of 2-(4-pentadecenylamino)benzoic 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. To the resulting oily residue of 2-(4-pentadecenylamino)benzoyl chloride hydrochloride is added, in one portion, the previously prepared mixture of sodium benzenesulfonamide in dimethylacetamide. The mixture is stirred for 30 minutes, without cooling, and is then filtered through a bed of diatomaceous earth. The filtrate is poured into 2 l. of water, and 250 ml. of saturated sodium chloride solution is added to coagulate the precipitate. The mixture is filtered and the product is washed with water and partially air dried. The product is dissolved in methylene chloride, the mixture is filtered through diatomaceous earth, and brine is added to break the emulsion. The layers are separated, the organic phase is dried over anhydrous sodium sulfate and filtered through a bed of 300 g. of hydrous magnesium silicate. The product is eluted with an additional 3 l. of methylene chloride. The first approximately 1 l. of filtrate is set aside and the remainder is evaporated to dryness. The residue is crystallized three times from toluene and the product is dried in the Abderhalden at 65° C. to provide the title compound as colorless crystals.

Workup

  1. temperaturecooling, to a suspension of 5.5 g
  2. stirringStirring
  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. additionTo the resulting oily residue of 2-(4-pentadecenylamino)benzoyl chloride hydrochloride is added, in one portion
  7. additionthe previously prepared mixture of sodium benzenesulfonamide in dimethylacetamide
  8. stirringThe mixture is stirred for 30 minutes
  9. temperaturewithout cooling
  10. filtrationis then filtered through a bed of diatomaceous earth
  11. additionThe filtrate is poured into 2 l
  12. additionof saturated sodium chloride solution is added
  13. filtrationThe mixture is filtered
  14. washthe product is washed with water and partially air
  15. customdried
  16. dissolutionThe product is dissolved in methylene chloride
  17. filtrationthe mixture is filtered through diatomaceous earth, and brine
  18. additionis added
  19. customThe layers are separated
  20. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  21. filtrationfiltered through a bed of 300 g
  22. washThe product is eluted with an additional 3 l
  23. customthe remainder is evaporated to dryness
  24. customThe residue is crystallized three times from toluene
  25. customthe product is dried in the Abderhalden at 65° C.

Sources & evidence

ORD record
ord-551baa237b7f44289b412fda457f7c98
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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