Dimethyl N-cyanodithioiminocarbonate → HCID 12889409, compound

HRID 894138Notes

Reaction equation

HRID 894138 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-c5a2929c74044b63bd8ddb6983c2e40c
Source dataset
uspto-grants-1981_08
Patent number
US04282363

Reaction notes

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