Sodium Hydroxide → HCID 15725747, compound

HRID 1460706Notes

Reaction equation

HRID 1460706 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30]([CH2:33][C:34]([O:36]C)=[O:35])(=[O:32])=[O:31])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30]([CH2:33][C:34]([OH:36])=[O:35])(=[O:32])=[O:31])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15725746HCID 15725746, compound

Product 1

HCID 15725747HCID 15725747, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]sulfonyl]acetate (0.94 g, 2 mmol), 3N sodium hydroxide solution (2.43 mL, 7 mmol) and methanol (100 mL) was heated at reflux. After 20 minutes, the methanol was removed in vacuo, the residue acidified with 1N HCl and extracted with dichloromethane. The organic phase was washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated to give a foam. Recrystallization from a mixture of dichloromethane and hexane (1:3) afford [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl) hexyl]sulfonyl]acetic acid (0.80 g, 88%); m.p.=153.5-155° C. MS(CI): m/e=459 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customthe methanol was removed in vacuo
  4. extractionextracted with dichloromethane
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a foam
  9. customRecrystallization
  10. additionfrom a mixture of dichloromethane and hexane (1:3)

Sources & evidence

ORD record
ord-753d5eaf06a842919c4abb4666cc3b70
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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