Ethanol → 4-Amino-2-methylbenzene-1-thiol

HRID 856760Notes

Reaction equation

HRID 856760 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[SH:11].C(O)C>C(O)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([SH:11])=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 107734502-Methyl-4-nitrobenzenethiol

Product 1

HCID 198673854-Amino-2-methylbenzene-1-thiolYield 31.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-methyl-4-nitrothiophenol (7.0 g) in acetic acid (100 ml) was added reduced iron (21.0 g) and the mixture was stirred for 40 hours. Ethanol was added to the mixture, and the insolubles were filtered off, and the solvent was distilled off under reduced pressure. To the obtained residue was added water, and the solution was neutralized with an aqueous solution of saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (hexane-ethyl acetate=3:1→hexane:ethyl acetate=0.2:1), to give 4-amino-2-methylthiophenol (1.8 g).

Workup

  1. filtrationthe insolubles were filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the obtained residue was added water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was separated
  8. custompurified by silica gel column chromatography (hexane-ethyl acetate=3:1→hexane:ethyl acetate=0.2:1)

Sources & evidence

ORD record
ord-88180d6cae5445b78e6629bc4fc625e5
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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