Sodium Iodide → HCID 14676632, compound

HRID 1164937Notes

Reaction equation

HRID 1164937 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.Cl[CH2:14][C:15](Cl)=[O:16].[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].[Na+].[I-]>CCO.O.C(O)(=O)C>[CH2:18]([N:20]([CH2:21][CH3:22])[CH2:14][C:15]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1)=[O:16])[CH3:19]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6577Chloroacetyl chlorideHCID 8021DiethylamineHCID 37325774-(Methylsulfonamido)aniline

Product 1

HCID 14676632HCID 14676632, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 100 mL of acetic acid under a nitrogen atmosphere add 12.9 g (69 mmol) of N-(4-aminophenyl)methanesulfonamide and 9.4 g (83 mmol) of chloroacetyl chloride. Stir the reaction mixture at ambient temperature. Monitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2MeOH, 19:1). Upon completion of the reaction, add 300 mL of H2O and suction filter the resulting solid. To 50 mL of EtOH is added 7.0 g (27 mmol) of the solid, 9.9 g (0.14 mol) of diethylamine, and 1 g of NaI. Stir the reaction mixture at ambient temperature. Monitor the progress of the reaction by thin-layer chromatography on silica gel (CHCl3 :MeOH, 9:1). Upon completion of the reaction remove the solvent in vacuo. To the resulting oil add 50 mL of H2O and 100 mL EtOAc. Separate the layers and dry the organic layer over anhydrous Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Chromatograph the resulting oil on 50 g of silica gel with CH2Cl2 :MeOH, 19:1. Combine the product fractions and remove the solvent in vacuo. Dissolve the residue in methanolic HCl and remove the solvent. Triturate the solid with EtOAc to afford the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2MeOH, 19:1)
  2. customUpon completion of the reaction
  3. filtrationfilter the resulting solid
  4. stirringStir the reaction mixture at ambient temperature
  5. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (CHCl3 :MeOH, 9:1)
  6. customUpon completion of the reaction remove the solvent in vacuo
  7. additionTo the resulting oil add 50 mL of H2O and 100 mL EtOAc
  8. customSeparate the layers
  9. dry with materialdry the organic layer over anhydrous Na2SO4
  10. customRemove the drying agent
  11. filtrationby filtration
  12. customremove the solvent in vacuo
  13. customCombine the product fractions and remove the solvent in vacuo
  14. dissolutionDissolve the residue in methanolic HCl
  15. customremove the solvent
  16. customTriturate the solid with EtOAc

Sources & evidence

ORD record
ord-c8aeed0e32ac4a10b4c0dedd42c81fe9
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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