Dimethylformamide → HCID 67322443, compound

Participants

Reaction Steps

4,5-Dimethyl-2-iodobenzamide (4f) was obtained from 4,5-dimethyl-2-iodobenzoic acid 4c in two steps. To a solution of 2-iodo-4,5-dimethylbenzo ic acid 4c (1.2 g, 4.34 mmol) in thionyl chloride (20 ml) was added a catalytic amount of DMF, and the resulting solution was heated to redox for 2-3 hours. Excess thionyl chloride was removed under reduced pressure, and the crude acid chloride was dissolved in dry THF (10 ml) and transferred to a pressure vessel. After the addition of 38% aqueous ammonium hydroxide (20 ml), the pressure vessel was sealed and the reaction stirred at room temperature for 12 h. The reaction mixture was then concentrated and diluted with water (75 ml). The product was filtered and washed with water followed by washing with hexanes, and drying (in vacuo) to give the amide 4f (75%) as solid. mp 195-197° C., 1H NMR (400 MHz, DMSO-d6): δ 2.15 and 2.16 (2s, 6H), 7.11 (s, 1H), 7.40 (s, 1H), 7.61 (s, 1H), 7.70 (s, 1H); 13C NMR (100 MHz, DMSO-d6): δ 19.23, 19.48, 90.12, 129.62, 136.92, 140.18, 140.26, 140.91, 171.25; HRMS (m/z): [M+H]+ calcd for C9H11INO, C9H11INO, 275.9880; found, 275.9878.

Provenance & Evidence