Water → HCID 57958525, compound

HRID 1502566Notes

Reaction equation

HRID 1502566 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=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:26]=[CH:25][N:24]=[CH:23][CH:22]=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 57958539HCID 57958539, compound

Product 1

HCID 57958525HCID 57958525, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

Into a 100 mL three-neck flask, 2.2 g (4.7 mmol) of 5,6-bis(4-bromophenyl)-3-(4-pyridyl)-1,2,4-triazine, 45 mL of para-xylene, 2.5 mL (23 mmol) of 2,5-Norbornadiene were put, and the solution was stirred at 140° C. for 14 hours under a nitrogen stream. After a certain time, water was added to the solution, and an aqueous layer was extracted with chloroform. The obtained extract was washed with a saturated saline together with the organic layer and then dried over magnesium sulfate. The obtained 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=2:1), so that 1.7 g of a target substance, yellow powder was obtained in a yield of 78%.

Workup

  1. extractionan aqueous layer was extracted with chloroform
  2. extractionThe obtained extract
  3. washwas washed with a saturated saline together with the organic layer
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe obtained mixture was subjected to gravity filtration
  6. concentrationthe obtained filtrate was concentrated
  7. customto give a solid
  8. customyellow powder was obtained in a yield of 78%

Sources & evidence

ORD record
ord-96f00ade821a485db39c69000b73be72
Source dataset
uspto-grants-2015_12
Patent number
US09209408B2

Reaction notes

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