Methyl isothiocyanate → Metiamide

HRID 1112023Notes

Reaction equation

HRID 1112023 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-16b78e24a9c44fdab089be10351e0b86
Source dataset
uspto-grants-1978_10
Patent number
US04119781

Reaction notes

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