Dimethyl N-cyanodithioiminocarbonate → N-cyano-S-methyl-N'-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethyl]isothiourea

HRID 329919Notes

Reaction equation

HRID 329919 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:6]=1)[CH3:3].[CH3:16][S:17][C:18](=[N:21][C:22]#[N:23])SC>C(O)C>[C:22]([NH:21][C:18](=[N:15][CH2:14][CH2:13][S:12][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:10]=[CH:9][N:8]=1)[S:17][CH3:16])#[N:23]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 132773272-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamine

Product 1

HCID 14771353N-cyano-S-methyl-N'-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethyl]isothioureaYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamine (1 g) in ethanol (10 ml) was added over 10 minutes to a solution of dimethylcyanodithioimidocarbonate (0.71 g) in ethanol (15 ml). The solution was stirred for 30 minutes, evaporated to dryness and the residue purified by elution from a column of silica gel with 7.5% methanol/chloroform to yield N-cyano-S-methyl-N'-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethyl]isothiourea (0.97 g) as a clear oil.

Workup

  1. customevaporated to dryness
  2. customthe residue purified by elution from a column of silica gel with 7.5% methanol/chloroform

Sources & evidence

ORD record
ord-e2dc5ad8023d4e099e127d50f7d6f98a
Source dataset
uspto-grants-1990_01
Patent number
US04894372

Reaction notes

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