Sodium Hydroxide → 4-(Butane-1-sulfonyl)-1-methyl-3,5-diphenyl-1H-pyrazole

HRID 1439138Notes

Reaction equation

HRID 1439138 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:16][C:17]1[C:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:19][N:20]([CH3:28])[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:13][CH2:14][CH3:15].[OH-:35].[Na+]>C(Cl)(Cl)Cl>[CH2:12]([S:16]([C:17]1[C:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:19][N:20]([CH3:28])[C:21]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:9])=[O:35])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 213980704-(Butylsulfanyl)-1-methyl-3,5-diphenyl-1H-pyrazole

Product 1

HCID 213981084-(Butane-1-sulfonyl)-1-methyl-3,5-diphenyl-1H-pyrazoleYield 61%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (10.15 g, 85%, 0.05 mole) in dry chloroform (100 ml) is added to 4-(n-butylthio)-1-methyl-3,5-diphenylpyrazole (6.5g, 0.02 mole) in dry chloroform (50 ml) and the reaction mixture stirred overnight at 10° C to 12° C. The mixture is poured into 10% aqueous sodium hydroxide (200 ml) and extracted with chloroform. The chloroform layer is separated, dried and stripped in vacuo to give a light-orange oil. The oil is chromatographed on silica gel with benzene. The fractions containing the product are combined, stripped in vacuo, extracted with methanol, filtered, stripped in vacuo and then recrystallized from hexane to give a white fluffy solid 4.37 g (61%), m.p. 92.5° C to 93° C.

Workup

  1. extractionextracted with chloroform
  2. customThe chloroform layer is separated
  3. customdried
  4. customto give a light-orange oil
  5. customThe oil is chromatographed on silica gel with benzene
  6. additionThe fractions containing the product
  7. extractionextracted with methanol
  8. filtrationfiltered
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-7c35cbc18cf44ec1a3c0e86fe4e251fc
Source dataset
uspto-grants-1977_11
Patent number
US04058391

Reaction notes

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