Pyrazole → 1-Tosylpyrozole

HRID 1785164ノート

反応式

HRID 1785164 の反応式
[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

参加物

5

反応物 3

HCID 1048PyrazoleHCID 6344DichloromethaneHCID 8623o-Toluenesulfonyl chloride

生成物 1

HCID 3207501-Tosylpyrozole収率 76%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8715fbe9663403b87216859031940bb
出典データセット
uspto-grants-2009_03
特許番号
US07504408B2

反応ノート

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