Dimethyl N-cyanodithioiminocarbonate → S-methyl-N-cyano-N'-[4-(5-methyl-4-imidazolyl)butyl]isothiourea

HRID 261625Notes

Reaction equation

HRID 261625 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH3:11].[CH3:12][S:13][C:14](=[N:17][C:18]#[N:19])SC>>[CH3:12][S:13][C:14](=[N:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH3:11])[NH:17][C:18]#[N:19]

Participants

3

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 127698424-(4-methyl-1H-imidazol-5-yl)butan-1-amine

Product 1

HCID 20394566S-methyl-N-cyano-N'-[4-(5-methyl-4-imidazolyl)butyl]isothioureaYield 75.3%

Procedure

Reaction of 4-(4-aminobutyl)-5-methylimidazole (see Example 7 (ii), 2.71 g, 0.012 mol) with dimethylcyanodithioimidocarbonate (1.75 g 0.013 mol), gave S-methyl-N-cyano-N'-[4-(5-methyl-4-imidazolyl)butyl]isothiourea (2.27 g) which was treated directly with methylamine to yield N-cyano-N'-methyl-N"[4-(5-methyl-4-imidazolyl)butyl]guanidine (1.35 g), m.p. 152°-154° C. (from acetonitrile).

Sources & evidence

ORD record
ord-2f14b43028bc44bba6393ecdfc34ca4c
Source dataset
uspto-grants-1979_08
Patent number
US04166184

Reaction notes

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