Methyl iodide → 2-Guanidino-4-[2-(2,3-dimethylisothioureido)ethylthiomethyl]thiazole hydrogen maleate hydriodide

HRID 67989Notes

Reaction equation

HRID 67989 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH:9]([C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][CH2:20][CH2:21][NH:22][C:23]([NH:25][CH3:26])=[S:24])[N:17]=1)[C:10]([NH2:12])=[NH:11].C[I:28]>C(O)C>[IH:28].[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH:9]([C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][CH2:20][CH2:21][NH:22][C:23](=[N:25][CH3:26])[S:24][CH3:1])[N:17]=1)[C:10]([NH2:12])=[NH:11]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178486119HCID 178486119, compound

Product 1

HCID 1784849862-Guanidino-4-[2-(2,3-dimethylisothioureido)ethylthiomethyl]thiazole hydrogen maleate hydriodide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-guanidino-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole hydrogen maleate (0.42 g.) in ethanol (15 ml.) was treated with methyl iodide (0.175 g.). The clear solution was heated under reflux on a steam bath for 1.5 hours, cooled and the volume reduced to 5 ml. by evaporation under reduced pressure. The insoluble material was filtered and recrystallized from ethanol to give 2-guanidino-4-[2-(2,3-dimethylisothioureido)ethylthiomethyl]thiazole hydrogen maleate hydriodide. Found: C, 30.2; H, 4.1; N, 14.8; S, 17.2. C14H23IN6O4S3 requires C, 29.94; H, 4.09; N, 14.97; S, 17.11%

Workup

  1. temperatureThe clear solution was heated
  2. temperatureunder reflux on a steam bath for 1.5 hours
  3. temperaturecooled
  4. customby evaporation under reduced pressure
  5. filtrationThe insoluble material was filtered
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5acae5530aeb4c17b5f366e505c913d7
Source dataset
uspto-grants-1982_08
Patent number
US04347370

Reaction notes

Loading…