Methyl iodide → HCID 67529325, compound

Participants

Reaction Steps

1.34 g (4.61 mmol) of 3-[2-amino-5-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazole-2(3H)-thione were solubilised in acetone (25 mL), then CH3I (10 eq, 2.87 mL) was added and the solution stirred at r.t. for 12 h. 3-[2-amino-5-(trifluoromethyl)phenyl]-4-methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide (3a) was recovered by filtration (white powder, 1.19 g, 60%) and by evaporation of the organic layer (776 mg, 39%). Mp 194° C.; 1H NMR (300 MHz, CD3OD) δ=2.27 (3H, d, J=1.1, CH3), 2.96 (3H, s, SCH3), 7.10-7.18 (1H, m, Ar), 7.62-7.70 (2H, m, Ar), 7.86 (1H, q, J=1.1, H5); 13C NMR (75 MHz, CD3OD) δ=13.74, 18.11, 118.28, 118.36, 118.68, 119.97 (q, J=34), 125.41 (q, J=270), 126.91 (q, J=4), 130.92 (q, J=4), 149.97, 148.73, 182.40; HRMS m/z C12H12N2F3S2 [M−I]+ calcd: 305.0388, found: 305.0389.

Provenance & Evidence