Hydrochloric Acid → HCID 178440347, compound

HRID 1155349Notes

Reaction equation

HRID 1155349 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([CH2:8][CH2:9][CH3:10])[NH:3]1.[OH-].[Ca+2].[OH-].[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=O.Cl>C1C=CC=CC=1.O1CCOCC1>[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([CH2:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[Cl:14])[C:4]([CH2:8][CH2:9][CH3:10])=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 691102-Chlorobenzoyl chlorideHCID 6093208Calcium HydroxideHCID 53871137HCID 53871137, compound

Product 1

HCID 178440347HCID 178440347, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

1.4 g. of 1-methyl-3-n-propyl-5-pyrazolone is dissolved in 10 ml. of dioxane with heating and then 1.5 g. of calcium hydroxide is added to the resulting solution. 1.75 g. of 2-chlorobenzoyl chloride is added dropwise with stirring at 50° C. 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 100 ml. of a 2 N hydrochloric acid solution is added thereto. The mixture is extracted with 70 ml. of chloroform and an organic layer is separated. The layer is washed with water, dried over anhydrous sodium sulfate and the solvent is distilled off from the layer to give 2 g. of brown oily residue. The residue thus obtained is dissolved in a small amount of benzene and adsorbed on a silica gel column, which is then eluted with benzene: ethanol (50:1) to give 0.6 g. of crystals. The crystals are recrystallized from methanol-water (7:3) to give 0.25 g. of the desired product as colorless columns having a melting point of 125°-126° C. Yield 9.2%

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. extractionThe mixture is extracted with 70 ml
  7. customof chloroform and an organic layer is separated
  8. washThe layer is washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent is distilled off from the layer
  11. customto give 2 g
  12. customThe residue thus obtained
  13. washis then eluted with benzene: ethanol (50:1)
  14. customto give 0.6 g
  15. customThe crystals are recrystallized from methanol-water (7:3)
  16. customto give 0.25 g

Sources & evidence

ORD record
ord-5cb5c99e213046d2a178b20b716b2d51
Source dataset
uspto-grants-1981_11
Patent number
US04301293

Reaction notes

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