Dimethylformamide → N-(1,3-dithiol-2-ylidene)-N-methyl-N-phenylammonium perchlorate

HRID 648907

Reaction equation

HRID 648907 reaction equation
CN(C)C=O.[Cl:6]([O-:10])(=[O:9])(=[O:8])=[O:7].CS[C:13]1[S:17][CH:16]=[CH:15][S+:14]=1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>CC(C)=O>[Cl:6]([O-:10])(=[O:9])(=[O:8])=[O:7].[S:14]1[CH:15]=[CH:16][S:17][C:13]1=[N+:19]([CH3:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7515N-MethylanilineHCID 8857Ethyl AcetateHCID 230390092-Methylthio-1,3-dithiolium perchlorate

Product 1

HCID 13854050N-(1,3-dithiol-2-ylidene)-N-methyl-N-phenylammonium perchlorateYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 2 ml of dimethylformamide, 2.0 g of 2-methylthio-1,3-dithiolium perchlorate was suspended, and 1.1 ml of N-methylaniline was gradually added thereto under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and then after an addition of 30 ml of ethyl acetate, the precipitated crystals were collected by filtration. The product was recrystallized from acetone, whereby 1.7 g (yield: 69%) of N-(1,3-dithiol-2-ylidene)-N-methyl-N-phenylammonium perchlorate (Compound No. 8) was obtained as crystals having a melting point of 169° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-99b16192a4ce4d59ba74bfc5f0be6098
Source dataset
uspto-grants-1988_04
Patent number
US04737494

Linked notes

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