Methyl iodide → N,N,N-trimethyl-o-nitrophenylmethanaminium iodide

HRID 473554

Reaction equation

HRID 473554 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])[CH3:3].[I:14][CH3:15]>C(Cl)Cl>[I-:14].[CH3:3][N+:2]([CH3:15])([CH3:1])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 420851N,N-dimethyl-2-nitrobenzylamine

Product 1

HCID 86676882N,N,N-trimethyl-o-nitrophenylmethanaminium iodideYield 167.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 57b (0.18 g, 0.5 mmol) and iodomethane (0.71 g, 5 mmol) in anhydrous CH2Cl2 (5 mL) was stirred for 12 h at r. t., then added additional iodomethane (0.71 g, 5 mmol) and continuously stirred for 12 h. After evaporation, the residue was dispensed with CH2Cl2 and filtered to give 58b (0.27 g, 84%) as yellow solid.

Workup

  1. stirringcontinuously stirred for 12 h
  2. customAfter evaporation
  3. filtrationfiltered

Sources & evidence

ORD record
ord-248a1c7ada74457faec3cfb183cb3ff4
Source dataset
uspto-grants-2014_01
Patent number
US08637490B2

Linked notes

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