Reaction equation
[CH2:1]([S:3]([NH2:6])(=[O:5])=[O:4])[CH3:2].[OH-].[Na+].[CH3:9]I.C[CH2:12][O:13]CC.[C:16](=[S:18])=[S:17]>CN(C)C=O.O.S(OS([O-])(=O)=O)([O-])(=O)=O.[C+4].S(OS([O-])(=O)=O)([O-])(=O)=O>[CH3:9][S:17](=[N:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[C:16](=[S:18])[O:13][CH3:12]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of ethanesulphonamide (12.0 g.) in dimethylformamide (75 ml.) at 4°, was added a solution of sodium hydroxide (4.45 g.) in water (6 ml.) and carbon disulphide (3.6 ml.) After stirring for 10 minutes at 5° sodium hydroxide (2.2 g.) in water (3 ml.) and carbon disulphate (1.5 ml) was added and after a further 10 minutes similar quantities of sodium hydroxide and carbon disulphide were again added. After stirring for 10 minutes at 5°, methyl iodide (42.6 g.) was added without external cooling and stirring was continued for 2 hours and the reaction mixture added to water (750 ml.) Extraction with ether and concentration yielded crude N-ethanesulphonyliminodithiocarbonic acid dimethyl ester (6.4 g.) This was reacted directly with 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (5.0 g.) and methylamine in ethanol by the method described in Example 7. The product was chromatographed on column of silica gel with ethyl acetate-ethanol (2:1) as eluant to yield N-ethanesulphonyl-N'-methyl-N"[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine as a glass (4.0 g.)
Workup
- additionwere again added
- temperaturewithout external cooling
- stirringstirring
- waitwas continued for 2 hours
Sources & evidence
- ORD record
- ord-b88bfe926afe43b39d3327a29f2245a2
- Source dataset
- uspto-grants-1978_12
- Patent number
- US04129657
Linked notes
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