Cyclohexane → 4-(Benzenesulfonyl)-1-methyl-3,5-diphenyl-1H-pyrazole

HRID 1658401Notes

Reaction equation

HRID 1658401 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([S:18][C:19]2[C:20]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:21][N:22]([CH3:30])[C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-:37].[Na+].C1CCCCC1>C(Cl)(Cl)Cl>[CH3:30][N:22]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:19]([S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:9])=[O:37])[C:20]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[N:21]1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 213980551-Methyl-3,5-diphenyl-4-(phenylsulfanyl)-1H-pyrazole

Product 1

HCID 213980834-(Benzenesulfonyl)-1-methyl-3,5-diphenyl-1H-pyrazoleYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
9 °C

Procedure

At a temperature of 9°C a solution of m-chloroperbenzoic acid (10.15 g, 85%, 0.05 mole) in dry chloroform (50 ml) is added to a solution of 4-(phenylthio)-1-methyl-3,5-diphenylpyrazole (6.84 g, 0.02 mole) in dry chloroform (50 ml). The reaction mixture is stirred for 3 hours at 9°C and then overnight at room temperature. A heavy precipitate forms. The mixture is treated with 2% aqueous sodium hydroxide and extracted with chloroform. The chloroform layer is separated and stripped in vacuo to give an oil. Trituration of the oil with cyclohexane affords crystals 6.8 g (91%), m.p. 135° to 141°C. Recrystallization from a mixture of benzene and pentane gave white crystals, m.p. 149° to 150°C.

Workup

  1. customovernight
  2. customat room temperature
  3. extractionextracted with chloroform
  4. customThe chloroform layer is separated
  5. customto give an oil

Sources & evidence

ORD record
ord-6157ccb8622e4f0c977333c2319ecd79
Source dataset
uspto-grants-1976_06
Patent number
US03963742

Reaction notes

Loading…