Methyl iodide → 2-Bromo-4-(methylthio)aniline

HRID 2072590Notes

Reaction equation

HRID 2072590 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([S:9][C:10]#N)[CH:6]=[CH:5][C:3]=1[NH2:4].[C-]#N.[Na+].CI>CO>[Br:1][C:2]1[CH:8]=[C:7]([S:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8929Sodium Cyanide2×HCID 38124212-Bromo-4-thiocyanatoaniline

Product 1

HCID 146018352-Bromo-4-(methylthio)aniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-bromo-4-thiocyanoaniline (11.5 g., 0.05 mole) and sodium cyanide (1.23 g., 0.025 mole) in methanol (100 ml.) is stirred at room temperature overnight. Sodium cyanide (0.025 mole) is then added and the reaction heated at reflux 2 hours and then cooled (0°-5° C.). Methyl iodide is added and stirring continued. Thin layer chromatography shows one product spot. Product is recovered by extraction with methylene chloride, 8.4 g.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux 2 hours
  3. temperaturecooled (0°-5° C.)
  4. customProduct is recovered by extraction with methylene chloride, 8.4 g

Sources & evidence

ORD record
ord-17ab256e09fa46588c1f0b202f82a60e
Source dataset
uspto-grants-1990_04
Patent number
US04913728

Reaction notes

Loading…