Benzenesulfonamide → 2-fluoro-4-(hexadecylamino)-N-(phenylsulfonyl)benzamide

HRID 1156124Notes

Reaction equation

HRID 1156124 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+].[F:13][C:14]1[CH:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].S(Cl)(Cl)=O>CC(N(C)C)=O.C(Cl)Cl.C(COC)OC>[F:13][C:14]1[CH:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:20]=[CH:19][C:15]=1[C:16]([NH:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])=[O:17]

Participants

8

Reactant 4

HCID 7370BenzenesulfonamideHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 205364112-Fluoro-4-(hexadecylamino)benzoic acid

Product 1

HCID 205364662-fluoro-4-(hexadecylamino)-N-(phenylsulfonyl)benzamide

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 during 30 minutes at room temperature. Stirring is continued for 30 minutes. In the meantime, a mixture of 36.2 g. of 2-fluoro-4-(hexadecylamino)benzoic acid in 100 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 and to the resulting oil residue is added, in one portion, the previously prepared mixture of sodium benzenesulfonamide in dimethylacetamide. The mixture is stirred for 30 minutes, without cooling, and then filtered. The filtrate is poured into 2 l. of water and 250 ml. of saturated sodium chloride solution. The product is collected by filtration and then 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 and evaporated. The residue is crystallined from toluene to yield 2-fluoro-4-(hexadecylamino)-N-(phenylsulfonyl)benzamide.

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 and to the resulting oil residue
  5. additionis added, in one portion
  6. additionthe previously prepared mixture of sodium benzenesulfonamide in dimethylacetamide
  7. stirringThe mixture is stirred for 30 minutes
  8. temperaturewithout cooling
  9. filtrationfiltered
  10. additionThe filtrate is poured into 2 l
  11. filtrationThe product is collected by filtration
  12. dissolutiondissolved in methylene chloride
  13. filtrationthe mixture is filtered through diatomaceous earth, and brine
  14. additionis added
  15. customThe layers are separated
  16. customthe organic phase is dried
  17. customevaporated

Sources & evidence

ORD record
ord-a936d250e363472f8debea509c0d5480
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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