Methyl isothiocyanate → N-methyl-N'-[2-((1,4-dimethyl-2-imidazolyl)methylthio)ethyl]thiourea

HRID 26828Notes

Reaction equation

HRID 26828 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[N:4]=[C:3]1[CH2:8][S:9][CH2:10][CH2:11][NH2:12].[CH3:13][N:14]=[C:15]=[S:16].C(OCC)(=O)C.C(O)C>C(O)C>[CH3:13][NH:14][C:15]([NH:12][CH2:11][CH2:10][S:9][CH2:8][C:3]1[N:2]([CH3:1])[CH:6]=[C:5]([CH3:7])[N:4]=1)=[S:16]

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 127889541,4-Dimethyl-2-[(2-aminoethyl)thiomethyl]imidazoleHCID 21584252Ethanol ethylacetate

Product 1

HCID 20557738N-methyl-N'-[2-((1,4-dimethyl-2-imidazolyl)methylthio)ethyl]thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction of 1,4-dimethyl-2-[(2-aminoethyl)thiomethyl]imidazole (derived from the 6.2 g. dihydrobromide) with methyl isothiocyanate (1.34 g.) in ethanol (50 ml.) followed by chromatography on a column of silica gel with ethyl acetate-ethanol (9:1) as eluant gave N-methyl-N'-[2-((1,4-dimethyl-2-imidazolyl)methylthio)ethyl]thiourea (2.1 g.). (Found: C, 46.8; H, 6.9; N, 21.5; S, 24.9. C10H18N4S2 requires: C, 46.5; H, 7.0; N, 21.7; S, 24.8).

Sources & evidence

ORD record
ord-d85917e71e1048b091f0101bc5754c44
Source dataset
uspto-grants-1979_04
Patent number
US04151288

Reaction notes

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