P-Xylene → HCID 57958496, compound

HRID 1502568Notes

Reaction equation

HRID 1502568 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N: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>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:27]=[CH:28][C:10]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N: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

5

Reactant 3

HCID 7809P-XyleneHCID 8473NorbornadieneHCID 57958487HCID 57958487, compound

Product 1

HCID 57958496HCID 57958496, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 200 mL three-neck flask were put 2.4 g (5.0 mmol) of 5,6-bis(4-bromophenyl)-3-(pyrimidin-2-yl)-1,2,4-triazine, 60 mL of para-xylene, 2.1 mL (19 mmol) of 2,5-Norbornadiene, and the mixture was refluxed under a nitrogen gas stream at 150° C. for 12 hours. After a certain time, water was added to the mixture, and an aqueous layer was extracted with toluene. The extract was washed with a saturated saline together with the organic layer, and the organic layer was then 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 recrystallized with chloroform/hexane, so that 1.6 g of a target substance, light-yellow solid was obtained in a yield of 67%.

Workup

  1. customIn a 200 mL three-neck flask were put
  2. extractionan aqueous layer was extracted with toluene
  3. washThe extract was washed with a saturated saline together with the organic layer
  4. dry with materialthe organic layer was then dried over magnesium sulfate
  5. filtrationThe mixture was subjected to gravity filtration
  6. concentrationthe obtained filtrate was concentrated
  7. customto give a solid
  8. customThe obtained solid was recrystallized with chloroform/hexane, so that 1.6 g of a target substance
  9. customlight-yellow solid was obtained in a yield of 67%

Sources & evidence

ORD record
ord-b6da0db7ff884962851a605c0c92c4d4
Source dataset
uspto-grants-2015_12
Patent number
US09209408B2

Reaction notes

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