Sodium ethoxide → HCID 178485061, compound

HRID 1200248Notes

Reaction equation

HRID 1200248 reaction equation
[Na].CC[O-].[Na+].[CH3:6][NH:7][C:8]([NH:12][CH2:13][CH2:14][SH:15])=[N:9][C:10]#[N:11].Cl.[CH3:17][N:18]([CH2:20][C:21]1[S:22][CH:23]=[C:24]([CH2:26]Cl)[N:25]=1)[CH3:19]>C(O)C>[CH3:6][NH:7][C:8]([NH:12][CH2:13][CH2:14][S:15][CH2:26][C:24]1[N:25]=[C:21]([CH2:20][N:18]([CH3:19])[CH3:17])[S:22][CH:23]=1)=[N:9][C:10]#[N:11]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 131219581-(4-(chloromethyl)thiazol-2-yl)-N,N-dimethylmethanamine hydrochlorideHCID 178485054HCID 178485054, compound

Product 1

HCID 178485061HCID 178485061, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

About 0.6 g of sodium were added to 50 ml. of dry ethanol under an N2 atmosphere, thus forming sodium ethylate in ethanol. 0.91 g of N-methyl-N'-(2-mercapto)ethyl-N"-cyanoguanidine (prepared by the procedure of U.S. Pat. No. 4,093,621) dissolved in 10 ml. of anhydrous ethanol was added thereto and the resulting mixture stirred at room temperature for about 1 hour. Next, 1.59 g of 2-dimethylaminomethyl-4-thiazolylmethylchloride hydrochloride was added thereto in portions over a 1 hour period. After the addition had been completed, the reaction mixture was stirred for an hour at room temperature and was then heated to refluxing temperature for an additional hour. The ethanol was removed from the reaction mixture by evaporation and ethyl acetate plus water (10:1) were added to the residue. The pH of the aqueous phase was adjusted to pH=8 with 1N aqueous hydrochloric acid. The ethyl acetate extract was separated and the ethyl acetate removed by evaporation. The residue was subjected to high pressure liquid chromatography (silica-20:80 ethanol/ethyl acetate). Fractions containing the desired product as shown by tlc were combined and the solvent evaporated therefrom. 1.10 g of N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N"-cyanoguanidine were obtained. The physical properties were substantially identical with those obtained in Example 4 for the same compound.

Workup

  1. dissolution4,093,621) dissolved in 10 ml
  2. waitin portions over a 1 hour period
  3. additionAfter the addition
  4. stirringthe reaction mixture was stirred for an hour at room temperature
  5. temperaturewas then heated
  6. temperatureto refluxing temperature for an additional hour
  7. customThe ethanol was removed from the reaction mixture by evaporation and ethyl acetate plus water (10:1)
  8. additionwere added to the residue
  9. extractionThe ethyl acetate extract
  10. customwas separated
  11. customthe ethyl acetate removed by evaporation
  12. additionFractions containing the desired product
  13. customthe solvent evaporated

Sources & evidence

ORD record
ord-419a864b39204e6babf6e00e1124506d
Source dataset
uspto-grants-1990_02
Patent number
US04904792

Reaction notes

Loading…