Methyl iodide → methyl 4-(pentylamino)-1H-imidazole-5-carbimidothioate

HRID 600601Notes

Reaction equation

HRID 600601 reaction equation
[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12](=[S:14])[NH2:13])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:15]I>CC(C)=O>[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]([S:14][CH3:15])=[NH:13])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 598538144-(pentylamino)-1H-imidazole-5-carbothioamide

Product 1

HCID 135984704methyl 4-(pentylamino)-1H-imidazole-5-carbimidothioateYield 112.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(pentylamino)-1H-imidazole-5-carbothioamide (1.0 g, 4.7 mmol) in acetone (40 mL) was added methyl iodide (0.80 g, 5.6 mmol) dropwise. The mixture was stirred at room temperature overnight. The solvent was removed and the residue was diluted with water and ethyl acetate. The organic layer was washed with water and brine, dried and concentrated to yield the crude product (1.2 g), which was used for next step without further purification. LCMS calculated for C10H19N4S (M+H): 227.1. found: 227.1.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with water and ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ecc3527c1c34e279b42c715cd9e8a2f
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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