Hydrochloric Acid → HCID 178429186, compound

HRID 477248Notes

Reaction equation

HRID 477248 reaction equation
Cl.[F:2][C:3]([F:21])([F:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([C:14]1[N:18]=[C:17]([NH2:19])[NH:16][N:15]=1)(=[O:13])=[O:12].[C:22](OCC)(=[O:27])[CH2:23][C:24]([CH3:26])=O>CO>[F:21][C:3]([F:2])([F:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([C:14]1[N:18]=[C:17]2[N:19]=[C:24]([CH3:26])[CH:23]=[C:22]([OH:27])[N:16]2[N:15]=1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 178509070HCID 178509070, compound

Product 1

HCID 178429186HCID 178429186, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1 ml of 12N hydrochloric acid in 250 ml of methanol was added to a mixture of 20.0 g (65.1 mmol) of N-(2-trifluoromethylphenyl)-5-amino-1,2,4-triazole-3-sulfonamide and 9.2 ml (72.2 mmol) of ethyl acetoacetate and the mixture heated to reflux with stirring. After about 5 days, most but not all of the starting material was found to have reacted by thin layer chromatography. The solution was chilled and the precipitate that formed was collected by filtration, washed with cold methanol and dried to obtain 16.5 g (67.9 percent of theory) of the title compound as a white solid hemihydrate melting at 245°-7° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux
  3. customto have reacted by thin layer chromatography
  4. temperatureThe solution was chilled
  5. customthe precipitate that formed
  6. filtrationwas collected by filtration
  7. washwashed with cold methanol
  8. customdried

Sources & evidence

ORD record
ord-f6a230b2756c4aadb216e4f784e4d47a
Source dataset
uspto-grants-1989_12
Patent number
US04886883

Reaction notes

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