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Pyridine → 6-bromo-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1513333
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HRID 1513333 반응식
C([N:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[C:6]([Br:12])=[N:5]1)(=O)C.N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1.CCOC(C)=O>[Br:12][C:6]1[C:7](=[O:11])[N:8]([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])[C:9](=[O:10])[NH:4][N:5]=1
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참가 물질

6

반응물 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 152295492-acetyl-6-bromo-2H-[1,2,4]triazine-3,5-dione

생성물 1

HCID 684307866-bromo-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione수율 46.7%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31275
1,4-Dioxane
용매

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온도
5 °C

실험 절차

2-acetyl-6-bromo-1,2,4-triazine-3,5(2H,4H)-dione (P6, 2.47 g, 10.56 mmol) was dissolved in 1,4-Dioxane (18 ml) and pyridine (2.56 ml, 31.7 mmol). The solution was cooled to 5° C. then benzoyl chloride (1.470 ml, 12.67 mmol) was added dropwise and the mixture was stirred at room temperature overnight. The day after the reaction mixture was diluted with AcOEt and washed with 0.5N HCl aq solution. Organic phase was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. Crude product (brown oil) was purified by flash chromatography (SiO2, eluent: Cy to Cy/AcOEt 6:4) affording 6-bromo-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione (1.46 g, 4.93 mmol, 46.7% yield) as a white powder.

후처리

  1. washwashed with 0.5N HCl aq solution
  2. customOrganic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customCrude product (brown oil) was purified by flash chromatography (SiO2, eluent: Cy to Cy/AcOEt 6:4)

출처 및 근거

ORD 기록
ord-bdefdbeffe234d45a9baf203bfcb8f58
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217168B2

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