Sodium Hydroxide → HCID 15725743, compound

HRID 1460704Notes

Reaction equation

HRID 1460704 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][CH2:31][C:32]([O:34]C)=[O:33])[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: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][CH2:31][C:32]([OH:34])=[O:33])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15725742HCID 15725742, compound

Product 1

HCID 15725743HCID 15725743, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]thio]acetate (1.01 g, 2 mmol), 3N sodium hydroxide solution (2.1 mL, 6 mmol) and methanol (125 mL) was heated at reflux for 20 minutes. The solvent was removed and the residue treated with 1N hydrochloric acid solution. Extraction with dichloromethane (three times) followed by drying of the organic phase over sodium sulfate and concentration in vacuo afforded an oil that crystallized on standing to give [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl) hexyl]thio]acetic acid (0.94 g, 96%); m.p.=92-97° C. MS(CI): m/e=471 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 minutes
  3. customThe solvent was removed
  4. additionthe residue treated with 1N hydrochloric acid solution
  5. extractionExtraction with dichloromethane (three times)
  6. dry with materialby drying of the organic phase over sodium sulfate and concentration in vacuo
  7. customafforded an oil that
  8. customcrystallized

Sources & evidence

ORD record
ord-9f04a0a8619047b79e5722cf6796dfdb
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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