Sodium Hydroxide → HCID 67794293, compound

HRID 1460708Notes

Reaction equation

HRID 1460708 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]([CH2:32][C:33]([O:35]C)=[O:34])=[O:31])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[OH2:31].[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: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]([CH2:32][C:33]([OH:35])=[O:34])=[O:31])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15725744HCID 15725744, compound

Product 1

HCID 67794293HCID 67794293, compoundYield 185%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]sulfinyl]acetate (1.06 g, 2.1 mmol), 3N sodium hydroxide solution (2.1 mL, 6.3 mmol) and methanol (50 mL) was heated at reflux for 10 minutes. The methanol was evaporated, the residue acidified to pH=5 with IN HCl and extracted with dichloromethane (3×). The combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated to afford [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]sulfinyl]acetic acid hydrate (0.98 g, 95%) as a white foam; m.p.=132.5°-134.5° C. MS(CI): m/e=443 (MH+ --CO2).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 minutes
  3. customThe methanol was evaporated
  4. extractionextracted with dichloromethane (3×)
  5. washThe combined extracts were washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5dd941a3a4954b8285f3250cd36ba3e3
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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