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

HRID 492446

반응식

HRID 492446 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-832d6a4c43fc4560886460dda4eb5781
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531557B2

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