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

HRID 249791Notes

Reaction equation

HRID 249791 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-905307b2581642a28643a59b8534f6bc
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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