Water → HCID 15725746, compound

HRID 1460705Notes

Reaction equation

HRID 1460705 reaction equation
[OH:1]OS([O-])=O.[K+].[C:7]1([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][S:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH2:42]>CO>[C:7]1([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][S:36]([CH2:37][C:38]([O:40][CH3:41])=[O:39])(=[O:1])=[O:42])[N:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15725742HCID 15725742, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 15725746HCID 15725746, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Oxone (potassium monopersulfate compound)(3.80 g, 6 mmol) suspended in water (20 mL) was added slowly to a stirred solution of methyl [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]thio]acetate (1.00 g, 2 mmol) in methanol (20 mL) maintained at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 5.5 hours before being poured onto water. The mixture was extracted with diethyl ether, the etheral layer washed twice with saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. Crystallization of the residue from a mixture of hexane and dichloromethane (25:1) afforded methyl [[6-(3,4,5-triphenyl 1H-pyrazol-1-yl)hexyl]sulfonyl]acetate (1.17 g, 91%); m.p.=92.5°-94.5° C. MS(CI): m/e=517 (MH+).

Workup

  1. temperatureto warm to room temperature
  2. additionbefore being poured onto water
  3. extractionThe mixture was extracted with diethyl ether
  4. washthe etheral layer washed twice with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customCrystallization of the residue
  8. additionfrom a mixture of hexane and dichloromethane (25:1)

Sources & evidence

ORD record
ord-bcf1c24842b846b8b0d76684097b84b0
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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