Methyl iodide → HCID 178512035, compound

HRID 499799Notes

Reaction equation

HRID 499799 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.[N:17]#[C:18][NH2:19].O.NN>CC#N>[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:19]\[C:18]#[N:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 9864CyanamideHCID 24654Hydrazine hydrate (1:1)HCID 86616333HCID 86616333, compound

Product 1

HCID 178512035HCID 178512035, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1-(4-iodophenyl)pyridine-2(1H)-thione (180 mg, 0.575 mmol) in CH3CN (15 mL), CH3I (0.50 mL, 8.0 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 CH3CN (5 mL). To the solution, cyanamide (200 mg, 4.76 mmol) and hydrazine monohydrate (0.100 mL, 2.06 mmol) were added. After being stirred at room temperature for 2 h, the mixture was purified by HPLC to give (E)-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)cyanamide (25 mg).

Workup

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

Sources & evidence

ORD record
ord-78e284f3339045caa9a014e899353d75
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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