Dimethylformamide → N-((1H-pyrrol-2-yl)methylene)-N-methylmethanaminium chloride

HRID 1037971Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

stirringThis reaction mixture was stirred at rt for 20 min
concentrationconcentrated to roughly half its volume
additionPetroleum ether (200 mL) was added
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-93579b527e8749cf972321a90c65e71e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546588B2

Reaction notes

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