HCID 877679, compound → 4-[(1-methyl-1H-imidazol-2-yl)thio]aniline

HRID 856783Notes

Reaction equation

HRID 856783 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([S:7][C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 877679HCID 877679, compoundHCID 5284359Calcium Chloride

Product 1

HCID 6096014-[(1-methyl-1H-imidazol-2-yl)thio]anilineYield 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

1-methyl-2-[(4-nitrophenyl)thio]imidazole (6.0 g), reduced iron (7.12 g) and calcium chloride (1.42 g) were added to 85% aqueous solution of ethanol (100 ml), and the mixture was stirred for 6 hours at 105° C. under nitrogen atmosphere. The mixture was allowed to be at room temperature, the insolubles were filtered off, and the solvent was distilled off under reduced pressure. To the obtained residue was added water and the mixture extracted with ethyl acetate twice. The organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was recrystallized from ethyl acetate-diisopropyl ether, to give 2-[(4-aminophenyl)thio]-1-methylimidazole (4.38 g) as yellow crystals.

Workup

  1. customto be at room temperature
  2. filtrationthe insolubles were filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionTo the obtained residue was added water
  5. extractionthe mixture extracted with ethyl acetate twice
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe obtained residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-e7ddde9dbc88476c8e8803ca3c6d77b4
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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