Methyl iodide → HCID 66930492, compound

HRID 1363036Notes

Reaction equation

HRID 1363036 reaction equation
[CH2:1]([N:3]([CH3:11])[C:4]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)=[O:5])[CH3:2].[CH3:12][I:13]>C(#N)C>[I-:13].[CH2:1]([N:3]([C:4]([NH+:6]1[CH:10]=[CH:9][N:8]([CH3:12])[CH2:7]1)=[O:5])[CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 25125284HCID 25125284, compound

Product 1

HCID 66930492HCID 66930492, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
22.5 °C

Procedure

To the cooled solution of N-ethyl-N-methyl-1H-imidazole-1-carboxamide (22.2 g, 145.25 mmol) in acetonitrile (40 mL) was charged slowly with methyl iodide (22.3 g, 157.4 mmol) while keeping internal temperature below 10° C. The reaction mixture was stirred at 20-25° C. for 2-3 hours and then it was evaporated under vacuum to yield 1-[[N-ethyl-(N-methyl)amino]carbonyl]-3-methyl-1H-imidazolium iodide. 1H NMR (CDCl3) δ 10.23 (s, 1H); 7.75 (s, 1H); 7.66 (s, 1H); 4.29 (s, 3H); 3.59 (q, J=7.2 Hz, 2H), 3.30 (s, 3H), 1.32 (t, J=7.2 Hz, 3H).

Workup

  1. customtemperature below 10° C
  2. customit was evaporated under vacuum

Sources & evidence

ORD record
ord-3192766290554ac8be89a9f9106065e3
Source dataset
uspto-grants-2011_02
Patent number
US07884121B2

Reaction notes

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