Dimethyl N-cyanodithioiminocarbonate → HCID 12889409, compound

HRID 1577923Notes

Reaction equation

HRID 1577923 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:13]([N:15]=[C:16](SC)[S:17][CH3:18])#[N:14]>CO>[C:13]([NH:15][C:16](=[N:12][CH2:11][CH2:10][S:9][CH2:8][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=1)[S:17][CH3:18])#[N:14]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 129515322-(3-Chloropyrid-2-ylmethylthio)ethylamine

Product 1

HCID 12889409HCID 12889409, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[(3-chloro-2-pyridyl)methylthio]ethylamine (5.77 g; 28.44 mmoles) and dimethyl cyanodithioimidocarbonate [prepared according to the procedure described in J. Org. Chem., 32, 1566 (1967)] (4.16 g; 28.44 mmoles) in methanol (50 ml) was stirred at ambient temperature under a positive pressure of nitrogen for 16 hours and then at reflux for 0.5 hours to complete the reaction. The reaction mixture was evaporated under reduced pressure and the crude product was recrystallized from isopropyl alcohol with activated carbon treatment to give N-cyano-N'-{2-[(3-chloro-2-pyridyl)methylthio]ethyl}-S-methylisothiourea; mp 119.5°-121°.

Workup

  1. temperatureat reflux for 0.5 hours
  2. customthe reaction
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe crude product was recrystallized from isopropyl alcohol with activated carbon treatment

Sources & evidence

ORD record
ord-9a32e1ac458149afa6acc6ab072db38b
Source dataset
uspto-grants-1981_09
Patent number
US04289876

Reaction notes

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