Sodium Hydroxide → N-(1,3-Dimethyl-1H-pyrazol-5-yl)-2-sulfanylbenzamide

HRID 2116794Notes

Reaction equation

HRID 2116794 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]C(=O)C2C=CC=CC=2)=[O:9])=[CH:5][C:4]([CH3:25])=[N:3]1.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CO>[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:9])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[SH:16])=[CH:5][C:4]([CH3:25])=[N:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 86610047thiobenzoic acid S-[2-(2,5-dimethyl-2H-pyrazol-3-ylcarbamoyl)-phenyl]ester

Product 1

HCID 69144537N-(1,3-Dimethyl-1H-pyrazol-5-yl)-2-sulfanylbenzamideYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The thiobenzoic acid S-[2-(2,5-dimethyl-2H-pyrazol-3-ylcarbamoyl)-phenyl]ester (as prepared in step 2 above; 0.966 g, 2.75 mmol) was dissolved in THF (50 mL) and MeOH (100 mL). Under N2(g), a 0.2M solution of NaOH (80 mL) was added and the mixture was stirred for 1.5 h at rt. A saturated solution of NaHCO3(aq) (100 mL) was added and the aqueous layer was extracted with CHCl3 (3×100 mL). The combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo. The crude mixture was then purified over silica (5% MeOH/CHCl3) to give the title compound in 67% yield (0.455 g, 1.84 mmol).

Workup

  1. extractionthe aqueous layer was extracted with CHCl3 (3×100 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude mixture was then purified over silica (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-215a561dc88f4b6f858790f307454526
Source dataset
uspto-grants-2008_10
Patent number
US07439371B2

Reaction notes

Loading…