Dimethyl N-cyanodithioiminocarbonate → HCID 178503877, compound

HRID 2166717Notes

Reaction equation

HRID 2166717 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[CH3:12][S:13][C:14](=[N:17][C:18]#[N:19])SC>C(O)C>[C:18]([NH:17][C:14](=[N:11][CH2:10][CH2:9][S:8][CH2:7][C:6]1[NH:5][CH:4]=[N:3][C:2]=1[CH3:1])[S:13][CH3:12])#[N:19]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 178433288HCID 178433288, compound

Product 1

HCID 178503877HCID 178503877, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(i) A solution of 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (23.4 g.) in ethanol was added slowly to a solution of dimethylcyanodithioimidocarbonate (20.0 g.) in ethanol, with stirring at room temperature. The mixture was set aside overnight at room temperature. Filtration afforded N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methylisothiourea (10.0 g.) m.p. 148°-150°. The filtrate was concentrated under reduced pressure and the mixture was triturated with cold water and the solid obtained, filtered off and recrystallised twice from isopropyl alcohol/ether to yield further product (27 g.), m.p. 148°-150°.

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-b6a4952b383148bb9feb74db6ae51787
Source dataset
uspto-grants-1983_06
Patent number
US04388319

Reaction notes

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