Sulfuric Acid → 5-(Benzenesulfinyl)-2-nitroaniline

HRID 616115Notes

Reaction equation

HRID 616115 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].C(OC(=O)C)(=[O:20])C.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+].C(OO)(=O)C.[OH-].[Na+]>CO.C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:20])[CH:5]=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 6585Peracetic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 1707372-Nitro-5-phenylthioanilineHCID 517045Sodium Acetate

Product 1

HCID 130355725-(Benzenesulfinyl)-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

10 G. of 1-amino-5-phenylthio-2-nitrobenzene in 100 ml. of acetic anhydride is treated with 0.25 ml. of concentrated sulfuric acid. The mixture is kept at 20°-25° C for 2 hours, then neutralized with sodium acetate and the solvent removed under vacuum. The residue is washed with water and methanol and dried. The resulting 1-acetamido-5-phenylthio-2-nitrobenzene is dissolved in 100 ml. of chloroform and treated at -30° C with a solution of peracetic acid (1 equivalent) in 10 ml. of methanol. The solution is warmed slowly to 20°-25° C and kept at the temperature for 12 hours, then washed successively with a solution of sodium bisulfite and a solution of sodium carbonate. Removal of the solvent leaves a gum which is treated with a mixture of 30 ml. of 5 N. sodium hydroxide and 60 ml. of methanol at 20°-25° C for 1 hour. Dilution with water followed by filtration of the product gives 1-amino-5-phenylsulfinyl-2-nitrobenzene which is purified by recrystallization from cyclohexane.

Workup

  1. customthe solvent removed under vacuum
  2. washThe residue is washed with water and methanol
  3. customdried
  4. dissolutionThe resulting 1-acetamido-5-phenylthio-2-nitrobenzene is dissolved in 100 ml
  5. temperatureThe solution is warmed slowly to 20°-25° C
  6. waitkept at the temperature for 12 hours
  7. washwashed successively with a solution of sodium bisulfite
  8. customRemoval of the solvent
  9. customleaves a gum which
  10. additionis treated with a mixture of 30 ml
  11. filtrationDilution with water followed by filtration of the product

Sources & evidence

ORD record
ord-c484745bc0704f35a98714a399c20f00
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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