Glycine, N-methyl-, ethyl ester → N-(1,3-dithiol-2-ylidene)-N-methyl-N-ethoxycarbonylmethylammonium perchlorate

HRID 648903Notes

Reaction equation

HRID 648903 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][NH:6][CH3:7])[CH3:2].[Cl:9]([O-:13])(=[O:12])(=[O:11])=[O:10].CS[C:16]1[S:20][CH:19]=[CH:18][S+:17]=1>O1CCCC1>[Cl:9]([O-:13])(=[O:12])(=[O:11])=[O:10].[S:17]1[CH:18]=[CH:19][S:20][C:16]1=[N+:6]([CH3:7])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:8]

Participants

4

Reactant 2

HCID 95849Glycine, N-methyl-, ethyl esterHCID 230390092-Methylthio-1,3-dithiolium perchlorate

Product 1

HCID 13854027N-(1,3-dithiol-2-ylidene)-N-methyl-N-ethoxycarbonylmethylammonium perchlorateYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 30 ml of tetrahydrofuran, 1.4 g of N-methylglycine ethyl ester was dissolved, and 2.0 g of 2-methylthio-1,3-dithiolium perchlorate was gradually added thereto under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and the precipitated crystals were collected by filtration and recrystallized from acetone-ethyl ether, whereby 1.7 g (yield: 67%) of N-(1,3-dithiol-2-ylidene)-N-methyl-N-ethoxycarbonylmethylammonium perchlorate (Compound No. 1) was obtained as crystals having a melting point of from 104° to 105° 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-292177b816964728b56bca4fa26889f8
Source dataset
uspto-grants-1988_04
Patent number
US04737494

Reaction notes

Loading…