Triethylamine → thiobenzoic acid S-[2-(2,5-dimethyl-2H-pyrazol-3-ylcarbamoyl)-phenyl]ester

HRID 2116793Notes

Reaction equation

HRID 2116793 reaction equation
[C:1]([S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CCN(CC)CC.[CH3:32][N:33]1[C:37]([NH2:38])=[CH:36][C:35]([CH3:39])=[N:34]1>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[CH3:32][N:33]1[C:37]([NH:38][C:12]([C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[S:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:14])=[CH:36][C:35]([CH3:39])=[N:34]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2595062-Benzoylsulfanylbenzoic acidHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Product 1

HCID 86610047thiobenzoic acid S-[2-(2,5-dimethyl-2H-pyrazol-3-ylcarbamoyl)-phenyl]esterYield 71%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-Benzoylsulfanyl-benzoic acid (as prepared in step 1 above; 1 g, 3.88 mmol) in anhydrous CH2Cl2 (40 mL), was added oxalyl chloride (2 mL, 22.5 mmol) followed by 2 drops of DMF. The suspension was stirred at room temperature until a clear solution was obtained. The solvent was evaporated under reduced pressure and the remaining crude solid was dissolved in anhydrous THF (40 mL). NEt3 (0.29 g, 2.5 mmol) and 2,5-Dimethyl-2H-pyrazol-3-ylamine (0.432 g, 3.88 mmol) were then added and the solution was allowed to stir at 50° C. overnight. The reaction mixture was diluted with EtOAc (60 mL) and extracted with H2O (3×50 mL) and saturated NaHCO3(aq). The organics were then dried over Na2SO4, filtered, concentrated in vacuo. The crude residue was purified via column chromatography (30% EtOAc/Hexanes) to give pure thiobenzoic acid S-[2-(2,5-dimethyl-2H-pyrazol-3-ylcarbamoyl)-phenyl]ester in 71% yield (0.966 g, 2.75 mmol).

Workup

  1. customwas obtained
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe remaining crude solid was dissolved in anhydrous THF (40 mL)
  4. stirringto stir at 50° C. overnight
  5. extractionextracted with H2O (3×50 mL) and saturated NaHCO3(aq)
  6. dry with materialThe organics were then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified via column chromatography (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ff30c0d2e29f4962812596bf947b607d
Source dataset
uspto-grants-2008_10
Patent number
US07439371B2

Reaction notes

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