Methyl iodide → HCID 178482153, compound

HRID 499801Notes

Reaction equation

HRID 499801 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=S)=[CH:4][CH:3]=1.CI.[CH3:17][NH2:18]>CC#N.CO>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10]/[C:9]/2=[N:18]\[CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 6329MethylamineHCID 86616333HCID 86616333, compound

Product 1

HCID 178482153HCID 178482153, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-iodophenyl)pyridine-2(1H)-thione (98 mg, 0.31 mmol) in CH3CN (5 mL), CH3I (0.25 mL, 4.0 mmol) was added. After being stirred at room temperature overnight, the mixture was concentrated in vacuo to give a solid. The solid was dissolved in MeOH (7 mL). To the solution, CH3NH2 (2M in THF, 0.80 mL, 1.6 mmol) was added. After being stirred at room temperature overnight, the mixture was purified by HPLC to give (E)-N-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)methanamine (59 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a solid
  3. stirringAfter being stirred at room temperature overnight
  4. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-369a253d00d24287a9ea46c8c4f63139
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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