Phenol → 2,3-Dicyano-5-chloro-6-phenoxypyrazine

HRID 128399

反応式

HRID 128399 の反応式
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6](Cl)=[C:5]([Cl:12])[N:4]=1)#[N:2].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O1CCCC1.O>[C:9]([C:8]1[C:3]([C:1]#[N:2])=[N:4][C:5]([Cl:12])=[C:6]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]=1)#[N:10]

参加物

6

反応物 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 6078205,6-Dichloro-2,3-dicyanopyrazine

生成物 1

HCID 128737532,3-Dicyano-5-chloro-6-phenoxypyrazine収率 50.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2,3-Dicyano-5,6-dichloropyrazine (1.00 g; 0.005 mole) was dissolved in 50 ml of tetrahydrofuran, and the solution was cooled to -15° to -10° C. A solution of 0.47 g (0.005 mole) of phenol and 0.21 g (0.005 mole) of sodium hydroxide in 25 ml of water was added dropwise over the period of 30 minutes. The mixture was stirred at -15° to -10° C. for 1 hour. The reaction mixture was poured into 100 ml of ice water, and the precipitate was collected by filtration. The precipitate was dissolved in 50 ml of chloroform, washed with 20 ml of a dilute aqueous solution of sodium hydroxide and 30 ml of water, dried over anhydrous calcium chloride, and concentrated under reduced pressure. The crude product was chromatographed on a column containing 60 g of silica gel using benzene as an eluent to afford 0.65 g (yield 50%) of 2,3-dicyano-5-chloro-6-phenoxypyrazine.

後処理

  1. temperaturethe solution was cooled to -15° to -10° C
  2. filtrationthe precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in 50 ml of chloroform
  4. washwashed with 20 ml of a dilute aqueous solution of sodium hydroxide and 30 ml of water
  5. dry with materialdried over anhydrous calcium chloride
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was chromatographed on a column
  8. additioncontaining 60 g of silica gel

出典と根拠

ORDレコード
ord-276f10414db04d1fac900c34d2062d94
出典データセット
uspto-grants-1981_03
特許番号
US04259489

関連ノート

読み込み中…