Chloroform → 2-Nitro-4-(propane-1-sulfinyl)aniline

HRID 1414757Notes

Reaction equation

HRID 1414757 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])(=O)C.C(Cl)(Cl)Cl.C(OO)(=[O:24])C.[OH-].[Na+]>CO>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][CH2:13][CH3:14])=[O:24])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6585Peracetic AcidHCID 14798Sodium HydroxideHCID 20362810N-[2-Nitro-4-(propylsulfanyl)phenyl]acetamide

Product 1

HCID 203628252-Nitro-4-(propane-1-sulfinyl)aniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

3.81 G. of 1-acetamido-2-nitro-4-n-propylthiobenzene in 35 ml. chloroform is treated at -20° to -15° C with a solution of 3.0 g. 40% peracetic acid in 3 ml. methanol. The mixture is allowed to warm to 20° C and stirred at 15°-25° C for four hours, then washed with sodium bisulfite solution and sodium bicarbonate solution. Removal of the chloroform leaves a gum which is treated on a steam bath, with 15 ml. 5N sodium hydroxide for one hour. The mixture is cooled, extracted with chloroform, separated and the solvent removed. The crude residue is recrystallized from benzene yielding 1-amino-2-nitro-4-n-propylsulfinylbenzene.

Workup

  1. washwashed with sodium bisulfite solution and sodium bicarbonate solution
  2. customRemoval of the chloroform
  3. customleaves a gum which
  4. additionis treated on a steam bath, with 15 ml
  5. temperatureThe mixture is cooled
  6. extractionextracted with chloroform
  7. customseparated
  8. customthe solvent removed
  9. customThe crude residue is recrystallized from benzene

Sources & evidence

ORD record
ord-0141d01fc0314915a1e7fc35d0d0e4ea
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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