Methyl iodide → 6-Ethynyl-2-(methylsulfanyl)-1,3-benzothiazole

HRID 1848001Notes

Reaction equation

HRID 1848001 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[S:9][C:5]=2[CH:4]=1)#[CH:2].[C:13]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[C:1]([C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([S:10][CH3:13])[S:9][C:5]=2[CH:4]=1)#[CH:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1784355876-Ethynylbenzo[d]thiazole-2-thiol

Product 1

HCID 866810266-Ethynyl-2-(methylsulfanyl)-1,3-benzothiazoleYield 139.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-ethynylbenzo[d]thiazole-2-thiol (4.0 g, 21 mmol) from Step 2 of this Example in 20 mL of DMF at 0° C. were added K2CO3 (7.25 g, 5.25 mmol), and MeI (5 mL). The mixture was stirred at rt for 2 h before it was partitioned between EtOAc and water, the organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 3:1 DCM/hexanes to afford 6-ethynyl-2-(methylthio)benzo[d]thiazole (1.5 g, 35%) as an off-white solid. LCMS (ESI) m/z 206 (M+H)+.

Workup

  1. customat 0° C.
  2. customwas partitioned between EtOAc and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 3:1 DCM/hexanes

Sources & evidence

ORD record
ord-40a5b781406145f5815f9eec6948f17a
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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