Methyl isothiocyanate → Metiamide

HRID 1287187Notes

Reaction equation

HRID 1287187 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

Procedure

A solution of 4-hydroxymethyl-5-methylimidazole hydrochloride (30.0 g) and cysteamine hydrochloride (23.0 g) in acetic acid (200 ml) was heated under reflux for 10 hours. Following cooling to 15°-20°, the solid which crystallised was collected and washed with isopropyl alcohol to give 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride m.p. 189°-192°. 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°. The product was collected and recrystallised from water to give N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea, m.p.150°-152°.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe solution was slowly cooled to 5°
  4. customThe product was collected
  5. customrecrystallised from water

Sources & evidence

ORD record
ord-6928ebadc12c438e9769b2dad738ef5a
Source dataset
uspto-grants-1976_10
Patent number
US03984293

Reaction notes

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