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

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)+.

1. filtrationThe solid was filtered off
2. washwashed with CH2Cl2
3. additionThe solid was treated with sat. aqueous NaHCO3 (10 mL)
4. extractionextracted with EtOAc (2×30 mL)
5. extractionThe organic extract
6. washwas washed with saturated NaCl (10 mL)
7. dry with materialdried over Na2SO4
8. filtrationThe solution was filtered
9. concentrationconcentrated in vacuo
10. customto give crude product as a yellow solid
11. customThis was purified by silica gel chromatography
12. washeluting with 50% CH2Cl2/hexanes

ORD record

ord-2077bf573de343fe920fd7dbed9d731c

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362241B2