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Triethylamine → 6-Fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile

HRID 392370
ノート
印刷プレビュー

反応式

HRID 392370 の反応式
Cl[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5](Cl)=[CH:6][N:7]=1.[F-:11].[K+].[CH3:13][CH:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C(N(CC)CC)C>CS(C)=O.O.C(OCC)(=O)C>[F:11][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([O:19][C:18]2[CH2:17][CH2:16][C:15](=[O:20])[C:14]=2[CH3:13])=[N:7][CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 130052-Methyl-1,3-cyclopentanedioneHCID 522689Potassium FluorideHCID 226628453,6-Dichloropyrazine-2-carbonitrile

生成物 1

HCID 226628306-Fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile収率 42.3%

試薬・触媒・溶媒 3

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

In 60 mL of dimethyl sulfoxide was dissolved 3.0 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 3.0 g of potassium fluoride, the mixture thus obtained was stirred at 90-100° C. for 2 hours. The reaction mixture was returned to room temperature, to which were successively added 2.1 g of 2-methyl-1,3-cyclopentandione and 7.2 ml of triethylamine. The mixture thus obtained was stirred at room temperature for one hour. The reaction mixture was added to a mixture of 50 mL of ethyl acetate and 200 mL of water, and the organic layer was separated. The organic layer thus obtained was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=2:1] to obtain 1.7 g of 6-fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile as a yellow-colored solid product.

後処理

  1. customthe mixture thus obtained
  2. customwas returned to room temperature, to which
  3. customThe mixture thus obtained
  4. stirringwas stirred at room temperature for one hour
  5. customthe organic layer was separated
  6. customThe organic layer thus obtained
  7. washwas washed successively with water and saturated aqueous solution of sodium chloride
  8. dry with materialdried on anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=2:1]

出典と根拠

ORDレコード
ord-784edebb176347d0ab6c64e54abfb226
出典データセット
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06800629B2

反応ノート

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