Water → HCID 57958576, compound

HRID 1502565Notes

Reaction equation

HRID 1502565 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)N=N[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[C:27]1(C)C=CC(C)=C[CH:28]=1.C12CC(C=C1)C=C2.O>C(OCC)(=O)C.CCCCCC>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:27]=[CH:28][C:10]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[N:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7809P-XyleneHCID 8473NorbornadieneHCID 57958579HCID 57958579, compound

Product 1

HCID 57958576HCID 57958576, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

Into a 200 mL three-neck recovery flask, 2.4 g (5.0 mmol) of 5,6-bis(4-bromophenyl)-3-(3-pyridyl)-1,2,4-triazine, 60 mL of para-xylene, and 2.5 mL (23 mmol) of 2,5-Norbornadiene were put. This solution was refluxed at 150° C. for 20 hours under a nitrogen stream. After a certain time, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extract was washed with a saturated saline together with an organic layer and the organic layer was dried over magnesium sulfate. The mixture was subjected to gravity filtration, and the obtained filtrate was concentrated to give a solid. The obtained solid was refined with silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized with chloroform/hexane, so that an objective substance, 0.68 g of yellow powder was obtained in a yield of 28%.

Workup

  1. extractionan aqueous layer was extracted with toluene
  2. extractionThe obtained extract
  3. washwas washed with a saturated saline together with an organic layer
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. filtrationThe mixture was subjected to gravity filtration
  6. concentrationthe obtained filtrate was concentrated
  7. customto give a solid
  8. customrecrystallized with chloroform/hexane, so that an objective substance

Sources & evidence

ORD record
ord-ae4f9e1c8a1e48a194b633da4bf467b8
Source dataset
uspto-grants-2015_12
Patent number
US09209408B2

Reaction notes

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