Hydrogen iodide → 2-Iodo-4-methyl-6-(methylthio)-1,3,5-triazine

Participants

Reaction Steps

A mixture of 2-chloro-4-methyl-6-(methylthio)-1,3,5-triazine (2110 mg, 12.01 mmol) and 67% hydriodic acid solution (2.260 mL, 30.0 mmol) in CH2Cl2 (4 mL) was stirred at room temperature for 3 h. The solid was filtered off and washed with CH2Cl2. The solid was treated with sat. aqueous NaHCO3 (10 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give crude product as a yellow solid. This was purified by silica gel chromatography eluting with 50% CH2Cl2/hexanes to give 2-iodo-4-methyl-6-(methylthio)-1,3,5-triazine (2.1 g, 7.86 mmol, 65.4% yield). 1H NMR (300 MHz, CDCl3) δ 2.53 (s, 3H); 2.51 (s, 3H). m/z (ESI, +ve ion) 267.8 (M+H)+.

Provenance & Evidence