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

HRID 426626Notes

Reaction equation

HRID 426626 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-c4ae7064a8924bd293ff321017edb949
Source dataset
uspto-grants-1979_10
Patent number
US04170652

Reaction notes

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