Dimethyl N-cyanodithioiminocarbonate → N-cyano-N'[2-(2-pyridylmethylthio)ethyl]-S-methylisothiourea

HRID 894129Notes

Reaction equation

HRID 894129 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[C:12]([N:14]=[C:15](SC)[S:16][CH3:17])#[N:13]>CO>[C:12]([NH:14][C:15](=[N:11][CH2:10][CH2:9][S:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[S:16][CH3:17])#[N:13]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 128894012-((2-Aminoethyl)thiomethyl)pyridine

Product 1

HCID 12889408N-cyano-N'[2-(2-pyridylmethylthio)ethyl]-S-methylisothiourea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[(2-pyridyl)methylthio]ethylamine (from the dihydrobromide, 20.0 g; 60.6 mmoles) and dimethyl cyanodithioimidocarbonate [prepared according to the procedure described in J. Org. Chem., 32, 1566 (1967)] (8.86 g; 60.6 mmoles) in methanol (150 ml) was stirred at ambient temperature under a positive pressure of nitrogen for 16 hours and then a reflux temperature for 0.5 hours to complete the reaction. The reaction mixture was evaporated under reduced pressure and the crude product was recrystallized from acetonitrile to give N-cyano-N'-{2-[(2-pyridyl)methylthio]-ethyl}-S-methylisothiourea; mp 85°-86.5° C.

Workup

  1. customthe reaction
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-df48f217724b4295adf5eda36102fb78
Source dataset
uspto-grants-1981_08
Patent number
US04282363

Reaction notes

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