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

HRID 2419760Notes

Reaction equation

HRID 2419760 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°. (Found: C, 28.8; H, 4.5; N, 14.8; S, 17.5; I, 33.8; C9H16N4S2 requires: C, 29.0; H, 4.6; N, 15.1; S, 17.2; I, 34.1%).

Workup

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

Sources & evidence

ORD record
ord-824b266a615f4a1381cbe62063031955
Source dataset
uspto-grants-1978_08
Patent number
US04107319

Reaction notes

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