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

HRID 1462304

반응식

HRID 1462304 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 128737532,3-Dicyano-5-chloro-6-phenoxypyrazine수율 50.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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 hyroxide 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.

후처리

  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 hyroxide 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

출처 및 근거

ORD 기록
ord-acb2143c4e3c4e6cb1fbadcb7d4bfd27
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04460403

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