Methyl iodide → HCID 550302, compound

HRID 732087Notes

Reaction equation

HRID 732087 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[CH3:7]I.[C:9](O)([C:11]([F:14])([F:13])[F:12])=O>CCO>[CH3:1][N:2]1[C:9]([C:11]([F:14])([F:13])[F:12])=[N:5][N:4]=[C:3]1[S:6][CH3:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 550302HCID 550302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methylthiosemicarbazid (10.0 g, 95.09 mmol) in TFA (46.7 ml) was heated to reflux o.n. Excess TFA was removed via evaporation. The residue was dissolved in aq. 1M NaOH (100 ml), followed by dropwise addition of CH3I (4.47 ml, 71.17 mmol) in EtOH (22 ml). The resulting mixture was stirred o.n. Partial evaporation of the solvent induced crystallization. After dilution with H2O the solid was collected via filtration and gave after drying the title compound (5.2 g, 28%). MS (M++1) 198

Workup

  1. temperatureto reflux o.n
  2. customExcess TFA was removed via evaporation
  3. dissolutionThe residue was dissolved in aq. 1M NaOH (100 ml)
  4. customPartial evaporation of the solvent induced crystallization
  5. filtrationAfter dilution with H2O the solid was collected via filtration
  6. customgave
  7. dry with materialafter drying the title compound (5.2 g, 28%)

Sources & evidence

ORD record
ord-c4bd093d6b4e4b9da1c1cef9a95e38fe
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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