Methyl iodide → 2-(Methylthio)benzoxazole

HRID 1446877Notes

Reaction equation

HRID 1446877 reaction equation
[SH:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][O-].[Na+].[Na].CI>CO>[CH3:11][S:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 41787732-(Methylthio)benzoxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2-Mercaptobenzoxazole (6.0 g, 0.04 mole) was slowly added, with stirring, to a solution of sodium methoxide prepared by the addition of sodium (1.0 g) to anhydrous methanol (150 ml). Methyl iodide (5 ml) was added and the mixture was stirred at a temperature of 50° C. for a period of 3 hours and allowed to stand overnight at room temperature. The methanol was removed by distillation under reduced pressure and the solid residue was triturated with ice water and the insoluble material was collected by filtration. The solid was dissolved in chloroform, dried over anhydrous magnesium sulfate and the solvent removed to give 2-(methylthio)benoxazole (5.8 g) as a brown oil.

Workup

  1. waitto stand overnight at room temperature
  2. customThe methanol was removed by distillation under reduced pressure
  3. customthe solid residue was triturated with ice water
  4. filtrationthe insoluble material was collected by filtration
  5. dissolutionThe solid was dissolved in chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent removed
  8. customto give 2-(methylthio)benoxazole (5.8 g) as a brown oil

Sources & evidence

ORD record
ord-cbd81648c3ae4dcc87f0a6953a89e87c
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

Loading…