Dimethyl malonate → HCID 178425409, compound

HRID 1031378Notes

Reaction equation

HRID 1031378 reaction equation
[Na].[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:4]=1[NH:11][S:12]([C:15]1[N:19]=[C:18]([NH2:20])[NH:17][N:16]=1)(=[O:14])=[O:13].[C:21](OC)(=[O:27])[CH2:22][C:23](OC)=[O:24]>C(O)C>[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:4]=1[NH:11][S:12]([C:15]1[N:19]=[C:18]2[N:20]=[C:21]([OH:27])[CH:22]=[C:23]([OH:24])[N:17]2[N:16]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 5360545SodiumHCID 178425411HCID 178425411, compound

Product 1

HCID 178425409HCID 178425409, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (3.11 g, 135 mmol) was added to 250 ml of absolute ethanol in a 500 ml round bottom flask and allowed to react under nitrogen. N-(2,6-dichloro-3-methylphenyl)-5-amino-1,2,4-triazole-3-sulfonamide (14.5 g, 45 mmol) and then dimethyl malonate (11.9 g, 90 mmol) were added and the mixture heated at reflux with stirring for about three days. The mixture was then cooled with an ice bath and filtered to collect the solids. These were washed with hexane and dissolved in about 75 ml of cold water and the resulting solution was acidified to about pH 2 with conc. hydrochloric acid. The precipitate that formed was collected by filtration and dried to obtain 13.55 g (77.1 percent of theory) of the title compound as a white powder, which decomposes above 200° C. This was shown to be the title compound by NMR.

Workup

  1. customto react under nitrogen
  2. temperaturethe mixture heated
  3. temperatureat reflux
  4. temperatureThe mixture was then cooled with an ice bath
  5. filtrationfiltered
  6. customto collect the solids
  7. washThese were washed with hexane
  8. dissolutiondissolved in about 75 ml of cold water
  9. customThe precipitate that formed
  10. filtrationwas collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-90d3e523efa1441b8e3835c88f1308f4
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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