Dimethyl malonate → HCID 178490216, compound

HRID 1031379Notes

Reaction equation

HRID 1031379 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[NH:14][S:15]([C:18]1[N:22]=[C:21]([NH2:23])[NH:20][N:19]=1)(=[O:17])=[O:16].[C:24](OC)(=[O:30])[CH2:25][C:26](OC)=[O:27]>C(O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:12])([F:13])[F:11])[C:5]=1[NH:14][S:15]([C:18]1[N:22]=[C:21]2[N:23]=[C:24]([OH:30])[CH:25]=[C:26]([OH:27])[N:20]2[N:19]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 5360545SodiumHCID 178490217HCID 178490217, compound

Product 1

HCID 178490216HCID 178490216, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (5.90 g, 257 mmol) was added to 250 ml of absolute ethanol under nitrogen and allowed to react. A 28.67 g, 85.0 mmol sample of N-(2-methoxy-6-trifluoromethylphenyl)-5-amino-1,2,4-triazole-3-sulfonamide and 24.46 g (170 mmol) of dimethyl malonate were added and the mixture heated at reflux with stirring for two days. It was then cooled with an ice bath and the solids present were collected by filtration and washed with hexane. They were then dissolved in about 150 ml of ice water and acidified with conc. hydrochloric acid to obtain 11.95 g, the title compound, which was collected by filtration and dried. The ethanolic solution was concentrated by evaporation and dried by adding toluene and removing volatiles by evaporation under reduced pressure three times. The residue was taken up in ethanol and treated as before with sodium and 16.85 g of dimethyl malonate to obtain another 10.26 g of the title compound. A total of 22.21 g (64.5 percent of theory) of the title compound, which melts at 237°-243° C. with decomposition, was obtained.

Workup

  1. customto react
  2. temperaturethe mixture heated
  3. temperatureat reflux
  4. temperatureIt was then cooled with an ice bath
  5. filtrationthe solids present were collected by filtration
  6. washwashed with hexane
  7. dissolutionThey were then dissolved in about 150 ml of ice water
  8. customto obtain 11.95 g
  9. filtrationthe title compound, which was collected by filtration
  10. customdried
  11. concentrationThe ethanolic solution was concentrated by evaporation
  12. customdried
  13. additionby adding toluene
  14. customremoving volatiles
  15. customby evaporation under reduced pressure three times
  16. additiontreated as before with sodium and 16.85 g of dimethyl malonate

Sources & evidence

ORD record
ord-ac3969a1b3a3445cb9076d69a6bbdf35
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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