Water → 1-[Diazo(trifluoromethanesulfonyl)methanesulfonyl]-4-methylbenzene

HRID 1837410ノート

反応式

HRID 1837410 の反応式
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][S:11]([C:14]([F:17])([F:16])[F:15])(=[O:13])=[O:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.S([N:29]=[N+:30]=[N-])(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C.O>C(#N)C>[C:1]1([CH3:18])[CH:2]=[CH:3][C:4]([S:7]([C:10]([S:11]([C:14]([F:16])([F:17])[F:15])(=[O:13])=[O:12])=[N+:29]=[N-:30])(=[O:9])=[O:8])=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 10756748HCID 10756748、化合物

生成物 1

HCID 226771391-[Diazo(trifluoromethanesulfonyl)methanesulfonyl]-4-methylbenzene

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

Crude p-toluenesulfonyl-trifluoromethanesulfonyl-methane (5 g, 0.017 mole) is dissolved in acetonitrile (200 ml) under nitrogen and the solution is cooled to 0° C. using an ice bath. Tosyl azide (16.3 g, 0.083 mole) and then triethylamine (4.6 ml, 0.063 mole) are added in one portion and the reaction mixture is stirred at that temperature for 24 h. After adding water (11), the mixture is extracted twice with dichloromethane (300 ml) and the combined organic phases are washed with 1 N HCl, saturated sodium bicarbonate and water. After drying over MgSO4 and removal of the solvent, the resulting yellow orange oil was chromatographed on silica gel using ethyl acetate/cyclohexane 1:5 as eluent, yielding p-toluenesulfonyl-trifluoromethanesulfonyl-diazomethane as a yellowish solid. The structure was confirmed by 1H/13C NMR and IR spectroscopy.

後処理

  1. extractionthe mixture is extracted twice with dichloromethane (300 ml)
  2. washthe combined organic phases are washed with 1 N HCl, saturated sodium bicarbonate and water
  3. dry with materialAfter drying over MgSO4 and removal of the solvent
  4. customthe resulting yellow orange oil was chromatographed on silica gel

出典と根拠

ORDレコード
ord-83b64730d54a474b8a684bb0629e3fd7
出典データセット
uspto-grants-2004_08
特許番号
US06783912B2

反応ノート

読み込み中…