HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1513333
Notes
Print preview

Reaction equation

HRID 1513333 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
5 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-bdefdbeffe234d45a9baf203bfcb8f58
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08217168B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes