Propanenitrile, 3-(methylamino)- → 1-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-cyanoethyl)ammonium iodide

HRID 648904Notes

Reaction equation

HRID 648904 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]#[N:6].[I-:7].CS[C:10]1[S:14][CH:13]=[CH:12][S+:11]=1>O1CCCC1>[I-:7].[S:11]1[CH:12]=[CH:13][S:14][C:10]1=[CH:1][NH2+:2][CH2:3][CH2:4][C:5]#[N:6]

Participants

4

Reactant 2

HCID 69656Propanenitrile, 3-(methylamino)-HCID 19751531(2H-1,3-Dithiol-2-ylidene)(methyl)sulfanium iodide

Product 1

HCID 867421011-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-cyanoethyl)ammonium iodideYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 30 ml of tetrahydrofuran, 0.8 g of N-methyl-(2-cyanoethyl)amine was dissolved, and 2.0 g of 2-methylthio-1,3-dithiolium iodide was gradually added thereto under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and then the precipitated crystals were collected by filtration and recrystallized from acetone-ethyl ether, whereby 1.8 g (yield: 80%) of 1-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-cyanoethyl)ammonium iodide (Compound No. 4) was obtained as crystals having a melting point of 203° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. filtrationthe precipitated crystals were collected by filtration
  3. customrecrystallized from acetone-ethyl ether

Sources & evidence

ORD record
ord-dea401f7c4c449dfb4db4bc414c93ab1
Source dataset
uspto-grants-1988_04
Patent number
US04737494

Reaction notes

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