Methyl iodide → 6-Iodo-2-(methylthio)benzo[d]thiazole

HRID 1691980Notes

Reaction equation

HRID 1691980 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI>O1CCCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([S:9][CH3:12])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178527793HCID 178527793, compound

Product 1

HCID 669058856-Iodo-2-(methylthio)benzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, room temperature mixture of 6-iodobenzo[d]thiazole-2-thiol (Reference Example 6a, 1.5 g, 5.1 mmol) and potassium carbonate (0.707 g, 5.1 mmol) in tetrahydrofuran (30 mL) was added methyl iodide (0.35 mL, 5.6 mmol). The reaction mixture was stirred at room temperature overnight, then volatiles were removed under reduced pressure to give a solid. The solid was partitioned between saturated aqueous sodium carbonate and chloroform. The chloroform layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to provide 6-iodo-2-(methylthio)benzo[d]thiazole. 1H NMR (300 MHz, CDCl3) δ ppm 2.78 (s, 3H), 7.58 (d, J=9 Hz, 1H), 7.69 (dd, J=2, 9 Hz, 1H), 8.07 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 308 (M+H)+.

Workup

  1. customvolatiles were removed under reduced pressure
  2. customto give a solid
  3. customThe solid was partitioned between saturated aqueous sodium carbonate and chloroform
  4. dry with materialThe chloroform layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a795a577bf73401c9dc0e86e1fbd6ba4
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

Loading…