Methyl isothiocyanate → Metiamide

HRID 461528Notes

Reaction equation

HRID 461528 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH3:9][C:10]1[N:11]=[CH:12][NH:13][C:14]=1[CH2:15][S:16][CH2:17][CH2:18][NH2:19].[CH3:20][N:21]=[C:22]=[S:23]>O>[CH3:20][NH:21][C:22]([NH:19][CH2:18][CH2:17][S:16][CH2:15][C:14]1[N:13]=[CH:12][NH:11][C:10]=1[CH3:9])=[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

Conditions

Temperature
5 °C

Procedure

Potassium carbonate (7.75 g.) was added to a solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride (14.6 g.) in water (120 ml.). The solution was stored at room temperature for 15 minutes and methyl isothiocyanate (5.15 g.) was added. After heating under reflux for 30 minutes, the solution was slowly cooled to 5° C. The product was collected and recrystallized from water to give N-methyl-N'-[2-((5-methyl-4-imidazolyl)-methylthio)ethyl]thiourea, m.p. 150°-152° C.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 30 minutes
  3. customThe product was collected
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-91b438b35fe445da9a4cf430fa471cbd
Source dataset
uspto-grants-1977_12
Patent number
US04063023

Reaction notes

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