Dimethyl N-cyanodithioiminocarbonate → HCID 12889409, compound

HRID 1413564Notes

Reaction equation

HRID 1413564 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-f6d9f318657c4dc384fba401b45cc42f
Source dataset
uspto-grants-1981_02
Patent number
US04250316

Reaction notes

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