Hydrochloric Acid → HCID 178429186, compound

HRID 619949Notes

Reaction equation

HRID 619949 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 chromatrography. The sollution 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 chromatrography
  4. temperatureThe sollution was chilled
  5. customthe precipitate that formed
  6. filtrationwas collected by filtration
  7. washwashed with cold methanol
  8. customdried

Sources & evidence

ORD record
ord-efd093c0a6cc48fe91d5e5270e623aec
Source dataset
uspto-grants-1989_04
Patent number
US04818273

Reaction notes

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