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Sodium Hydroxide → N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-pyridine-2-sulphonamide

HRID 1062742
Notes
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Reaction equation

HRID 1062742 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)(=[O:23])=[O:22])[N:10]([CH3:30])[N:9]=1)(=O)C.[OH-].[Na+]>O1CCOCC1>[OH:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[C:11]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)(=[O:22])=[O:23])[N:10]([CH3:30])[N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22282030N-[3-(2-acetoxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-pyridine-2-sulfonamide

Product 1

HCID 22281891N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-pyridine-2-sulphonamideYield 59.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To N-[3-(2-acetoxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazole-5-yl]-2-pyridine sulfonamide (Preparation 35) (1.05 g) in dioxan (10 ml) was added 1N NaOH (aq.) (5.34 ml). The mixture was stirred at 50° C. for 1 hour. The reaction was concentrated under reduced pressure to low volume and then partitioned between ethyl acetate (20 ml) and water (15 ml). The aqueous layer was separated and acidified to pH 6 with 2N hydrochloric acid (aq.). the product was extracted with ethyl acetate (2×20 ml), washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with solvent gradient, pentane:ethyl acetate (4:6 to 0:1, by volume) to yield the title compound as a colourless foam (560 mg).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure to low volume
  2. custompartitioned between ethyl acetate (20 ml) and water (15 ml)
  3. customThe aqueous layer was separated
  4. extractionthe product was extracted with ethyl acetate (2×20 ml)
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel eluting with solvent gradient, pentane:ethyl acetate (4:6 to 0:1, by volume)

Sources & evidence

ORD record
ord-8457fee81b2b40bfbd6481159c42af0d
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06962923B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes