Pyrazole → 1-Tosylpyrozole

HRID 1785164

반응식

HRID 1785164 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[CH2:7]Cl.[C:9]1(C)[C:10]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1>N1C=CC=CC=1>[CH3:7][C:13]1[CH:14]=[CH:9][C:10]([S:15]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)(=[O:16])=[O:17])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 1048PyrazoleHCID 6344DichloromethaneHCID 8623o-Toluenesulfonyl chloride

생성물 1

HCID 3207501-Tosylpyrozole수율 76%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of pyrazole (2 g, 29.0 mmol), dichloromethane (20 ml) and pyridine (5 ml) was added 4 toluene sulphonyl chloride (6.89 g, 36 mmol) and the reaction mixture stirred at ambient temperature for 1 hour. The reaction mixture was partitioned between dichlormethane and an aqueous solution of sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue as purified by flash chromatography on silica eluting with a mixture of 70-100% dichloromethane in hexane and then 10% ethyl acetate in dichloromethane to give the product as a white solid (4.9 g, 76%). NMR Spectrum: (CDCl3) 2.43 (s, 3H), 6.39 (m, 1H), 7.34 (d, 2H), 7.72 (d, 1H), 7.89 (d, 2H), 8.10 (d, 1H). Mass Spectrum: M+H+ 223 and M+H− 221.

후처리

  1. customThe reaction mixture was partitioned between dichlormethane
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue as purified by flash chromatography on silica eluting with a mixture of 70-100% dichloromethane in hexane

출처 및 근거

ORD 기록
ord-e8715fbe9663403b87216859031940bb
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504408B2

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