Ammonium Chloride → HCID 68501979、化合物

HRID 570831ノート

反応式

HRID 570831 の反応式
[CH3:1][Si:2]([CH:5]=[N+:6]=[N-:7])([CH3:4])[CH3:3].C([Li])CCC.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=[C:19](C#N)[C:20]#[N:21].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]1[C:19]([C:20]#[N:21])=[N:7][NH:6][C:5]=1[Si:2]([CH3:4])([CH3:3])[CH3:1]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 341752-(Thiophen-2-yl)malononitrileHCID 167693TrimethylsilyldiazomethaneHCID 178418339Butyllithium

生成物 1

HCID 68501979HCID 68501979、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒2 回

実験手順

After a solution of trimethylsilyldiazomethane in hexane (0.6 mol/L, 5 mL) was added to tetrahydrofuran (20 mL) under an argon atmosphere, to this reaction mixture was added a solution of n-butyl lithium in hexane (2.6 mol/L, 1.08 mL) in a dropwise manner over 5 minutes at −78° C., and this mixture was stirred at same temperature for 20 minutes. And then to this reaction mixture was added a solution of 2-thiophene-2-ylmethylene malononitrile (0.32 g) in tetrahydrofuran (5 mL) in a dropwise manner over 20 minutes. To this reaction mixture was added saturated aqueous ammonium chloride solution, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. This residue was washed with hexane to give 4-thiophene-2-yl-5-trimethylsilanyl-1H-pyrazole-3-carbonitrile (0.496 g). To the 4-thiophene-2-yl-5-trimethylsilanyl-1H-pyrazole-3-carbonitrile were added methanol (20 mL) and 1.0 mol/L aqueous sodium hydroxide solution (20 mL), and this mixture was heated to reflux for 2 hours. This reaction mixture was acidified (pH1) with adding 1.0 mol/L hydrochloric acid, the precipitated solid was collected by filtration. This obtained solid was washed with water, dried under reduced pressure at 50° C. to give the title compound (0.154 g).

後処理

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washThis residue was washed with hexane

出典と根拠

ORDレコード
ord-cf4dc6c23b7e4e0dbe00f95e12fa334c
出典データセット
uspto-grants-2015_05
特許番号
US09023882B2

反応ノート

読み込み中…