4-Toluenesulfonyl chloride → 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 559729

반응식

HRID 559729 반응식
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[H-].[Na+].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1COCC1.[NH4+].[Cl-]>[CH2:9]([O:8][C:6]([C:4]1[CH:5]=[N:1][N:2]([S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:3]=1)=[O:7])[CH3:10]

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 142179ethyl 1H-pyrazole-4-carboxylate

생성물 1

HCID 216282771-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

To a solution of ethyl 1H-pyrazole-4-carboxylate (4.50 g, 32.11 mmol) in THF was added 60% NaH (1.60 g, 40.00 mmol) in mineral oil. After 20 minutes, p-toluenesulfonyl chloride was added. After 3 hours, the mixture was diluted with saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 30-50% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester.

후처리

  1. waitAfter 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 30-50% ethyl acetate in heptane
  8. concentrationthe solvent was concentrated in vacuo

출처 및 근거

ORD 기록
ord-c6c1caf4f0554cc580b27e0f9d6a773a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063065B2

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