Methyl isothiocyanate → Metiamide

HRID 2286743Notes

Reaction equation

HRID 2286743 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[NH2:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[N:15]=[CH:16][NH:17][C:18]=1[CH3:19].[CH3:20][N:21]=[C:22]=[S:23]>O>[CH3:20][NH:21][C:22]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[N:15]=[CH:16][NH:17][C:18]=1[CH3:19])=[S:23]

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 11430Potassium CarbonateHCID 30159992-(((5-Methyl-1H-imidazol-4-yl)methyl)thio)ethylamine dihydrochloride

Product 1

HCID 1548992Metiamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (7.75 g.) was added to a solution of 14.6 g. of 4-(2-aminoethyl)thiomethyl-5-methylimidazole dihydrochloride in 120 ml. of water. The solution was maintained at ambient temperature for 15 minutes and 5.15 g. of methyl isothiocyanate was added. After heating under reflux for 0.5 hour, the solution was slowly cooled to 5°. The product was collected and recrystallized from water to give N-methyl-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]thiourea, m.p. 150°-152°.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 0.5 hour
  3. temperaturethe solution was slowly cooled to 5°
  4. customThe product was collected
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-cd38c8d960b842f1b34b5e8044adda2a
Source dataset
uspto-grants-1981_05
Patent number
US04267337

Reaction notes

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