Water → 1-Pyrid-2-yl-2-methylsulphonyl-4-phenyl-pyrazolin-5-one

HRID 1382204Notes

Reaction equation

HRID 1382204 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11](=[O:12])[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][NH:8]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11](=[O:12])[C:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:9][N:8]1[S:27]([CH3:26])(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 135904734-Phenyl-2-(pyridin-2-yl)-1,2-dihydro-3H-pyrazol-3-one

Product 1

HCID 137867791-Pyrid-2-yl-2-methylsulphonyl-4-phenyl-pyrazolin-5-oneYield 71.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

23.7 g (0.1 mole) of 1-pyrid-2-yl-4-phenyl-pyrazolin-5-one are dissolved in 200 ml of dioxane. After addition of 10.1 g (0.1 mole) of triethylamine, 11.5 g (0.1 mole) of methanesulphonyl chloride are added dropwise at room temperature, while cooling gently. The mixture is subsequently stirred at room temperature for a further 2 hours and at 70° C. for 5 hours, cooled and stirred into 1 l of water. The crystals are filtered off with suction, dried in air and recrystallized from ethanol. 22.5 g (71% of theory) of 1-pyrid-2-yl-2-methylsulphonyl-4-phenyl-pyrazolin-5-one of melting point 112°-114° C. are obtained.

Workup

  1. additionare added dropwise at room temperature
  2. temperaturewhile cooling gently
  3. temperaturecooled
  4. filtrationThe crystals are filtered off with suction
  5. customdried in air
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-bdb0565fe646497b876a3bc59c53b61b
Source dataset
uspto-grants-1989_02
Patent number
US04806540

Reaction notes

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