Reaction #94226

Reaction equation

N-n-propanesulphonyliminodithiocarbonic acid dimethyl ester

N-n-propanesulphonyliminodithiocarbonic acid

4-methyl-5-((2-aminoethyl)thiomethyl)imidazole

methylamine

n-propanesulphonamide

sodium hydroxide

methyliodide

→

N-methyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-n-propanesulphonylguanidine

Solvents

ethanol hexane

carbon disulphide

Conditions

Workup

1. 1
   Otherfollowed by chromatographic purification on a column of silica gel with ethyl acetate-ethanol (4:1) as eluant

Procedure

Reaction of n-propanesulphonamide with sodium hydroxide, carbon disulphide and methyliodide by the method described in Example 8 afforded N-n-propanesulphonyliminodithiocarbonic acid dimethyl ester, m.p. 73°-74° (from ethanol-hexane). (Found: C, 31.7; H, 5.7; N, 6.2; S, 42.0. C6H13NO2S3 requires: C, 31.7; H, 5.8; N, 6.2; S, 42.3) (b) The reaction of N-n-propanesulphonyliminodithiocarbonic acid (4.7 g.) dimethyl ester with 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (3.5 g.) and methylamine by the method described in Example 7 followed by chromatographic purification on a column of silica gel with ethyl acetate-ethanol (4:1) as eluant afforded N-methyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-n-propanesulphonylguanidine as a glass (5.0 g.).

Source