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

HRID 2116793ノート

反応式

HRID 2116793 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ff30c0d2e29f4962812596bf947b607d
出典データセット
uspto-grants-2008_10
特許番号
US07439371B2

反応ノート

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