Trifluoroacetic anhydride → 5-Chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide

HRID 627690ノート

反応式

HRID 627690 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[N:4][CH:3]=1.C(N)(N)=[O:14].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[N+:4]([O-:14])[CH:3]=1

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 57992035Methyl 6-chloro-3-methylpyrazine-2-carboxylate

生成物 1

HCID 867281445-Chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of methyl 6-chloro-3-methylpyrazine-2-carboxylate (8.6 g, 46.1 mmol) and hydrogen peroxide urea adduct (8.1 g, 86 mmol) in dichloromethane (100 mL) was added 2,2,2-trifluoroacetic anhydride (10.9 ml, 78 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with DCM and quenched with water. The aqueous layer was extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the crude product 5-chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (8.83 g, 43.6 mmol, 95% yield) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 8.31 (1H, s), 4.02 (3H, s), 2.65 (3H, s).

後処理

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-744bd9f5361c4e71aefcf0cae120cc6f
出典データセット
uspto-grants-2016_04
特許番号
US09309263B2

反応ノート

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