Methyl iodide → 2-(Methylthio)benzo[d]oxazol-6-ol

HRID 1922196Notes

Reaction equation

HRID 1922196 reaction equation
[SH:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:12](N(CC)CC)C.CI>C(Cl)Cl>[CH3:12][S:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178515778HCID 178515778, compound

Product 1

HCID 210778082-(Methylthio)benzo[d]oxazol-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the 2-mercaptobenzo[d]oxazol-6-ol (1.55 g, 9.28 mmol, 1.0 eq) in 20 mL of methylene chloride was added triethylamine (1.87 g, 18.56 mmol, 2.0 eq) and methyl iodide (1.77 g, 13.92 mmol, 1.5 eq) at room temperature. The reaction mixture was stirred at rt for 3 hours. The mixture was diluted with 100 mL of methylene chloride. The resulting mixture was washed with water (10 mL), brine (10 mL), then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by silica gel column eluted with ethyl acetate and hexane to give the titled compound. MH+=182.

Workup

  1. washThe resulting mixture was washed with water (10 mL), brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give crude product, which
  6. customwas purified by silica gel column
  7. washeluted with ethyl acetate and hexane

Sources & evidence

ORD record
ord-b14d9dadae954fbea9a8ae637288170c
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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