p-Toluenesulfonic acid → HCID 13279459, compound

HRID 620915Notes

Reaction equation

HRID 620915 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][C:21]([CH3:25])=[N:20]2)[CH:16]=[CH:17][CH:18]=1.[OH-].[Na+]>O>[Cl:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH:22]=[C:21]([CH3:25])[N:20]2[CH3:1])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 666562-(3-Chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 13279459HCID 13279459, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

90 g of p-toluenesulfonic acid was added to 50 g of 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one [Chemical Abstracts Registry Number (90-31-3)], and the resulting mixture was stirred on an oil bath at 150° C. for 2.5 hours. The reaction mixture was allowed to cool down to 100° C. or less. A solution prepared from 25 g of sodium hydroxide and 150 ml of water was added dropwise thereto. After adding thereto 350 ml of water, the mixture was extracted with chloroform. The chloroform phase was separated and then dried over anhydrous potassium carbonate. After insoluble materials were filtered off, the filtrate was concentrated to dryness to obtain 28.1 g of 1-(3-chlorophenyl)-2,3-dimethyl-3-pyrazolin-5-one. When recrystallization was carried out from ethyl acetate, crystals having a melting point of 98° to 100° C. were obtained.

Workup

  1. temperatureto cool down to 100° C. or less
  2. additionwas added dropwise
  3. additionAfter adding
  4. extraction350 ml of water, the mixture was extracted with chloroform
  5. customThe chloroform phase was separated
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationAfter insoluble materials were filtered off
  8. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8f6d656521f24ab38e2322465bebfefc
Source dataset
uspto-grants-1989_04
Patent number
US04822891

Reaction notes

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