[CH3:1][N:2]([CH:4]=O)[CH3:3].C(Cl)(=O)C([Cl:9])=O.[NH:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1>C(Cl)Cl>[Cl-:9].[NH:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:4]=[N+:2]([CH3:3])[CH3:1]A solution of DMF (60.0 mL, 738 mmol) in DCM (60 mL) was added to a stirred solution of oxalyl chloride in DCM (60 mL) at 0° C. The mixture was stirred at 0° C. for 20 min then a solution of pyrrole (45.0 g, 666 mmol) in DCM (150 mL) was added over 15 min. This reaction mixture was stirred at rt for 20 min and concentrated to roughly half its volume. Petroleum ether (200 mL) was added and the precipitate was collected by filtration to give N-((1H-pyrrol-2-yl)methylene)-N-methylmethanaminium chloride (90.0 g, 80%). 1H NMR (DMSO-d6, 400 MHz) δ 13.23 (s, 1H), 8.65 (s, 1H), 7.79 (s, 1H), 7.45 (s, 1H), 6.68 (q, J=1.6 Hz, 1H), 3.70 (s, 3H), 3.64 (s, 3H).
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