Methyl iodide → HCID 22461311, compound

Participants

Reaction Steps

To a stirred solution of 6,6-dimethyl-2-thiocyanato-4,5,6,7-tetrahydro-1H-indol-4-one (400 mg, 1.8 mmol) and MeI (124 μL, 2.0 mmol) in MeOH (10 mL) at −5° C. was added a solution of KOH (117 mg, 2.1 mmol) in 1:1 MeOH/water (6 mL), maintaining the temperature below 0° C. The mixture was stirred for 3 h at room temperature, after which time the MeOH was removed and the residue partitioned between DCM and water. The organic layer was separated and the aqueous phase re-extracted with DCM. The combined organic layers were dried (Na2SO4) and evaporated to afford the title compound (350 mg, 88%) as a colourless solid. mp 195-196° C. Found: C, 62.20; H, 7.13; N, 6.34%. Calc. C11H15NOS.0.2(H2O): C, 62.06; H, 7.29; N, 6.58%. 1H NMR (360 MHz, d6-DMSO) δ 1.02 (6H,s), 2.19 (2H,s), 2.34 (3H,s), 2.61 (2H,s), 6.30 (1H,d, J=2.4 Hz), 11.59 (1H,br s). MS (ES+) 210 (M+1).

Provenance & Evidence