2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1055983-02-2

HRID 883516Notes

Reaction equation

HRID 883516 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:10][N:9]=2)=[N:6][CH:7]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:12][N:13]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54759228HCID 54759228, compound

Product 1

HCID 575524811055983-02-2Yield 81.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(5-aminopyridin-2-yl)-6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine (0.950 g, 3.8 mmol) in anhydrous toluene (25 mL) under N2 was added 2,3-dichloro-5,6-dicyanobenzoquinone (1.7 g, 7.5 mmol). The reaction mixture was allowed to reflux and stir for 12 hr. The reaction mixture was concentrated under reduced pressure, and the crude residue was concentrated in vacuo onto deactivated silica gel and chromatographed using a gradient (0-100%) of acetone in hexanes to give 771 mg (3.1 mmol, 81%) of the title compound as a red solid, mp 207-209° C.

Workup

  1. temperatureto reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. concentrationthe crude residue was concentrated in vacuo
  4. customchromatographed

Sources & evidence

ORD record
ord-e37bd4e7bb8241c390c958161185debd
Source dataset
uspto-grants-2012_08
Patent number
US08236949B2

Reaction notes

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