Hydrochloric Acid → HCID 178434075, compound

HRID 1155347Notes

Reaction equation

HRID 1155347 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[NH:3]1.[OH-].[Ca+2].[OH-].[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13].Cl>O1CCOCC1>[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:23][CH:22]=2)[C:4]([CH3:8])=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 27668471,3-dimethyl-1H-pyrazol-5-olHCID 6093208Calcium Hydroxide

Product 1

HCID 178434075HCID 178434075, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 22 ml. of dry dioxane is dissolved 2.24 g. of 1,3-dimethyl-5-pyrazolone and then 2.96 g. of calcium hydroxide is added thereto. 3.71 g. of p-nitrobenzoyl chloride is added dropwise thereto while stirring at room temperature. After completion of the dropwise addition, the mixture is heated under reflux for 1 hour. After completion of the reaction, the reaction mixture is allowed to cool and then 40 ml. of a 2 N hydrochloric acid solution is added thereto. Crystalline substances thus separated are recovered by filtration and washed with water to give 4.38 g. of crude crystals. This product is recrystallized from methanol to give 3.62 g. of the desired product as pale yellow columns having a melting point of 234°-235° C. Yield 69.3%

Workup

  1. additionAfter completion of the dropwise addition
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 1 hour
  4. customAfter completion of the reaction
  5. temperatureto cool
  6. customCrystalline substances thus separated
  7. filtrationare recovered by filtration
  8. washwashed with water
  9. customto give 4.38 g
  10. customThis product is recrystallized from methanol
  11. customto give 3.62 g

Sources & evidence

ORD record
ord-4d72b2c8394749d3a46ffa47369e3a43
Source dataset
uspto-grants-1981_11
Patent number
US04301293

Reaction notes

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