Methanol → methyl N'-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydroiodide

HRID 893982Notes

Reaction equation

HRID 893982 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[S:13].[CH3:15][I:16].CO>CC(C)=O>[IH:16].[CH3:15][S:13][C:12](=[NH:14])[NH:11][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 6328Methyl iodideHCID 127186972-((4-Methyl-5-imidazolyl)methylthio)ethylthiourea

Product 1

HCID 178504045methyl N'-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydroiodideYield 62.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-thiourea (2.29 g) and methyl iodide (1.56 g) in acetone (45 ml) containing methanol (5 ml) was left at room temperature for 18 hours. Concentration followed by recrystallisation from isopropyl alcohol-petroleum ether (b.p. 60/80°) gave the title compound (2.3 g) m.p. 128°-131°.

Workup

  1. concentrationConcentration
  2. customfollowed by recrystallisation from isopropyl alcohol-petroleum ether (b.p. 60/80°)

Sources & evidence

ORD record
ord-9a68d09435b145c8b66b25d38251b08f
Source dataset
uspto-grants-1981_08
Patent number
US04282234

Reaction notes

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