Hydrochloric Acid → 98594-08-2

HRID 266567Notes

Reaction equation

HRID 266567 reaction equation
Cl.[CH3:2][S:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH3:13].O.C(=O)([O-])[O-].[Na+].[Na+]>CO.[Fe]>[CH3:13][C:5]1[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=1[S:3][CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 53715611HCID 53715611, compound

Product 1

HCID 5439611398594-08-2Yield 41.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (128 ml) was added slowly to a suspension of 2-methylsulphenyl-4-nitrotoluene (36.6 g) in methanol. Iron powder (36 g) was added with stirring whilst maintaining the temperature below 50° C. The mixture was stirred at room temperature for 4 hours. The mixture was poured into water neutralized (by the addition of sodium carbonate), filtered and the residue was extracted with dichloromethane. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with aqueous sodium chloride solution, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica eluted with a mixture of ethyl acetate and n-hexane to give 4-methyl-3-methylsulphenylaniline (12.8 g) as an orange solid, NMR (CDCl3) 2.2(s,3H), 2.35 (s,3H), 3.45 (s,2H), 6.1-6.9 (m,3H).

Workup

  1. temperaturewhilst maintaining the temperature below 50° C
  2. stirringThe mixture was stirred at room temperature for 4 hours
  3. filtrationfiltered
  4. extractionthe residue was extracted with dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. washthe combined organic layers were washed with aqueous sodium chloride solution
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by column chromatography on silica
  11. washeluted with a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-0dcefb1de16a46ab8c71c63c923d0dd2
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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