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

HRID 2116793노트

반응식

HRID 2116793 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff30c0d2e29f4962812596bf947b607d
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439371B2

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