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

HRID 2040956Notes

Reaction equation

HRID 2040956 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-b2624aa6f49a4c4c93c64e914b269489
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

Loading…