Methyl iodide → HCID 178492112, compound

HRID 559563Notes

Reaction equation

HRID 559563 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][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>CC#N.CN(C=O)C>[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:25]\[C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 7732P-AnisidineHCID 86616333HCID 86616333, compound

Product 1

HCID 178492112HCID 178492112, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-iodophenyl)pyridine-2(1H)-thione (192 mg, 0.61 mmol) in CH3CN (5 mL), CH3I (0.40 mL, 6.4 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 DMF (3 mL). To the solution, p-anisidine (317 mg, 2.6 mmol) was added. After being stirred at 100° C. overnight, the mixture was purified by HPLC to give (E)-N-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)-4-methoxybenzenamine (90 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a solid
  3. stirringAfter being stirred at 100° C. overnight
  4. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-ffcc7d35ee3642f2b407a052652372f8
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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