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Acrolein → 3-[6-bromo-3,5-dioxo-4-(phenylcarbonyl)-4,5-dihydro-1,2,4-triazin-2(3H)-yl]propanal

HRID 1513334
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HRID 1513334 반응식
[Br:1][C:2]1[C:3](=[O:17])[N:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[C:5](=[O:8])[NH:6][N:7]=1.C(N(CC)CC)C.[CH:25]([CH:27]=[CH2:28])=[O:26]>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:17])[N:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[C:5](=[O:8])[N:6]([CH2:28][CH2:27][CH:25]=[O:26])[N:7]=1
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참가 물질

5

반응물 3

HCID 7847AcroleinHCID 8471TriethylamineHCID 684307866-bromo-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione

생성물 1

HCID 594961013-[6-bromo-3,5-dioxo-4-(phenylcarbonyl)-4,5-dihydro-1,2,4-triazin-2(3H)-yl]propanal수율 103.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirring solution of 6-bromo-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione (1.46 g, 4.93 mmol) in dry N,N-Dimethylformamide (DMF) (64.9 ml), TRIETHYLAMINE (0.825 ml, 5.92 mmol) was added and the mixture was stirred at room temperature for 15 minutes. Acrolein (0.366 ml, 4.93 mmol) was then added and the mixture was left stirring at room temperature for 3 hours. It was then quenched with NH4Cl saturated solution and diluted with AcOEt. Phases were separated, organic phase was washed with cold water, dried over sodium sulphate, filtered and concentrated under reduced pressure affording 3-[6-bromo-3,5-dioxo-4-(phenylcarbonyl)-4,5-dihydro-1,2,4-triazin-2(3H)-yl]propanal (1.8 g, 5.11 mmol). The compound was used for next step without purification.

후처리

  1. waitthe mixture was left
  2. stirringstirring at room temperature for 3 hours
  3. customIt was then quenched with NH4Cl saturated solution
  4. additiondiluted with AcOEt
  5. customPhases were separated
  6. washorganic phase was washed with cold water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1e5a3f621314420d8a2a733929c3a82b
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217168B2

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