Hydrochloric Acid → HCID 178429188, compound

HRID 619948Notes

Reaction equation

HRID 619948 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][S:11]([C:14]1[N:18]=[C:17]([NH2:19])[NH:16][N:15]=1)(=[O:13])=[O:12].[C:20](OCC)(=[O:25])[CH2:21][C:22]([CH3:24])=O.Cl>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][S:11]([C:14]1[N:18]=[C:17]2[N:19]=[C:22]([CH3:24])[CH:21]=[C:20]([OH:25])[N:16]2[N:15]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 178425411HCID 178425411, compound

Product 1

HCID 178429188HCID 178429188, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 32.2 g (0.10 mol) of N-(2,6-dichloro-3-methylphenyl)-5-amino-1,2,4-triazole-3-sulfonamide and 14 ml (0.11 mol) of ethyl acetoacetate in 500 ml of methanol containing 1 ml of 12N hydrochloric acid was heated to reflux with stirring for about 18 hours. The solid present was collected by filtration and the filtrate was heated to reflux for another day. The mixture obtained was cooled in an ice bath and the solid present was collected by filtration. The filtrate was concentrated to about 200 ml by evaporation of methanol and heated to reflux overnight. The mixture obtained was filtered to collect the solid present. The filtrate was concentrated to about 150 ml, treated with about 2 ml of ethyl acetoacetate, and heated at reflux for about 3 days. The solids present were collected by filtration and dried to obtain 6.4 g, 10.0 g, 8.2 g and 11.1 g crops of the title compound for a total of 35.7 g (92 percent of theory). The first obtained crop melted at 346°-7° C. with decomposition.

Workup

  1. temperatureto reflux
  2. filtrationThe solid present was collected by filtration
  3. temperaturethe filtrate was heated
  4. temperatureto reflux for another day
  5. customThe mixture obtained
  6. temperaturewas cooled in an ice bath
  7. filtrationthe solid present was collected by filtration
  8. concentrationThe filtrate was concentrated to about 200 ml by evaporation of methanol
  9. temperatureheated
  10. temperatureto reflux overnight
  11. customThe mixture obtained
  12. filtrationwas filtered
  13. customto collect the solid present
  14. concentrationThe filtrate was concentrated to about 150 ml
  15. additiontreated with about 2 ml of ethyl acetoacetate
  16. temperatureheated
  17. temperatureat reflux for about 3 days
  18. filtrationThe solids present were collected by filtration
  19. customdried

Sources & evidence

ORD record
ord-44250fce3e3c4035b4e94a4b8f5e8a0b
Source dataset
uspto-grants-1989_04
Patent number
US04818273

Reaction notes

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