1-Methylimidazole → HCID 178480884, compound

Participants

Reaction Steps

1-Methyl-3-(3-(triphenylphosphonio)propyl)-1H-imidazol-3-ium bromide was synthesized by refluxing the mixture of 1-methyl-1H-imidazole and (3-bromopropyl)triphenylphosphonium bromide (1:1) in ethanol for 12 h; after cooling down, the solvent was removed and the crude product was washed with ethyl acetate. Then the white product was treated with silver (I) oxide in CH2Cl2 for 12 h, and the crude Ag—NHC product was filtered and washed with CH2Cl2 and then with diethyl ether, and was used for the next step directly. The procedure for the synthesis of 3 is similar to that for 1. Total yield 32%; 1H NMR (400 MHz, CD3CN, 25° C.): δ=8.21 (t, J=8.0 Hz, 1H), 7.82 (m, 3H), 7.69-7.72 (m, 3H), 7.66 (d, J=2.0 Hz, 1H), 7.55-7.63 (m, 12H), 7.17 (d, J=0.9 Hz, 2H), 6.98 (d, J=0.9 Hz, 2H), 4.57 (t, J=7.1 Hz, 2H), 3.94 (s, 3H), 3.27 (m, 2H), 2.11 (m, 2H); FAB-MS: m/z 940 [M−OTf]+; Elemental Analysis calcd (%) for C38H33AuF6N7O6PS2.H2O: C, 41.20; H, 3.18; N, 8.85; found: C, 41.25; H, 3.29; N, 8.72.

Provenance & Evidence