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

HRID 1701143Notes

Reaction equation

HRID 1701143 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-2b539e646df24f68b61300959dfa9ad5
Source dataset
uspto-grants-1980_03
Patent number
US04191769

Reaction notes

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