Sodium Hydroxide → HCID 67794293, compound

HRID 982077Notes

Reaction equation

HRID 982077 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-lH-pyrazol-1-yl)hexyl]sulfinyl]acetate (1.06 g, 2.1 mmol), 3 N 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 (3x). The combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated to afford [[6-(3,4,5-triphenyl-lH-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 (3x)
  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-86f49997772f44569cdb9ac1710c466e
Source dataset
uspto-grants-1991_02
Patent number
US04994482

Reaction notes

Loading…