Hydrogen Peroxide → 5-(4-[1,3]Dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carboxamide

HRID 492446ノート

反応式

HRID 492446 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[N:12]=[CH:13][C:14]([C:17]#[N:18])=[N:15][CH:16]=2)=[C:8]([CH3:21])[CH:7]=1.C([O-])([O-])=[O:23].[K+].[K+].OO>CS(C)=O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[N:12]=[CH:13][C:14]([C:17]([NH2:18])=[O:23])=[N:15][CH:16]=2)=[C:8]([CH3:21])[CH:7]=1

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 597300525-(4-[1,3]Dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carbonitrile

生成物 1

HCID 597302765-(4-[1,3]Dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carboxamide収率 137.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Take up 5-(4-[1,3]dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carbonitrile (0.082 g, 0.305 mmol) and K2CO3 (0.020 g, 0.152 mmol) in DMSO (3.0 mL). Add 30% H2O2 (0.090 mL, 0.792 mmol) and stir at room temperature for 1.5 hours before quenching with water (10 mL). Extract with ethyl acetate (50 mL). Wash the organic layer with water (1× 10 mL), dry over Na2SO4, filter and concentrate. Purify by flash chromatography, eluting with 40% ethyl acetate in dichloromethane to give the title compound (0.063 g, 68.6%): MS ES+ 302.0 (M+H)+; TLC [silica gel 60 F254, 40% ethyl acetate in dichloromethane] Rf=0.17.

後処理

  1. custombefore quenching with water (10 mL)
  2. extractionExtract with ethyl acetate (50 mL)
  3. washWash the organic layer with water (1× 10 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by flash chromatography
  8. washeluting with 40% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-832d6a4c43fc4560886460dda4eb5781
出典データセット
uspto-grants-2009_05
特許番号
US07531557B2

反応ノート

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