Methyl iodide → 7-Bromo-2-(methylthio)benzo[d]oxazole

HRID 469822Notes

Reaction equation

HRID 469822 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8]([SH:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:12]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[C:10]2[O:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178527769HCID 178527769, compound

Product 1

HCID 674568117-Bromo-2-(methylthio)benzo[d]oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 g (26.1 mmol) 7-bromo-benzooxazole-2-thiol, 7.28 g (52.2 mmol) K2CO3, 4.1 g (28.7 mmol) MeI in 80 ml DMF is stirred at room temperature for 1 h. The reaction mixture is then poured on water and extracted 2× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo to afford the title compound.

Workup

  1. additionThe reaction mixture is then poured on water
  2. extractionextracted 2× with EtOAc
  3. washThe combined organic layers are washed with water and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-c25e223ba1c24721a93ba704c882b175
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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