Hydrochloric Acid → HCID 178479520, compound

HRID 1700733Notes

Reaction equation

HRID 1700733 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:16][C:15]2[NH:14][N:13]=[C:12]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[C:10](=O)[CH2:9]1.[C:25]([NH:28][NH2:29])([NH2:27])=[NH:26].Cl.Cl.O>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:16][C:15]2[NH:14][N:13]=[C:12]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[C:10](=[N:29][NH:28][C:25]([NH2:27])=[NH:26])[CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317564HCID 18317564, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178479520HCID 178479520, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(2-chlorophenyl)-3-phenylamino-4,5,6,7-tetrahydroindazol-4-one (0.4 g), aminoguanidine hydrochloride (0.16 g), concentrated hydrochloric acid (0.31 ml), water (0.31 ml) and ethanol (20 ml) was refluxed for 6 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution to make the solution alkaline. The mixture was extracted with ethylacetate, and the organic layer was washed with water and concentrated under reduced pressure. The residue was dissolved in ethanol, and to the solution was added 1N hydrochloric acid (5 ml) and concentrated. Precipitated crystals were recrystallized from ethanol to give 6-(2-chlorophenyl)-4-guanidinoimino-3-phenylamino-4,5,6,7-tetrahydroindazole hydrochloride (Compound 146) (0.23 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue was added sodium hydrogen carbonate solution
  4. extractionThe mixture was extracted with ethylacetate
  5. washthe organic layer was washed with water
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol
  8. additionto the solution was added 1N hydrochloric acid (5 ml)
  9. concentrationconcentrated
  10. customPrecipitated crystals
  11. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-8780e1aff4444394b9eb1414f46cb4ec
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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