2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 135973970, compound

HRID 1165149Notes

Reaction equation

HRID 1165149 reaction equation
[OH:1][C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(O)(=O)C.C1C=CC=CC=1>[OH:1][C:2]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19862543HCID 19862543, compound

Product 1

HCID 135973970HCID 135973970, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 241BenzeneSolvent2×

Procedure

300 mg of 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)imidazole are heated to about 60°-70° on a water-bath together with 10 drops of glacial acetic acid in 25 ml of benzene. After the dropwise addition of a solution of 250 mg of dicyanodichlorobenzoquinone in 10 ml of benzene, the mixture is warmed for an additional 15 minutes. The reaction mixture is subsequently cooled in an ice-bath and the separated solid is removed by filtration. The filtrate is shaken with 10% sodium carbonate solution. After separation of the organic phase the aqueous phase is extracted once with benzene. The combined organic phases are dried with anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The crystalline residue is recrystallized from ethyl acetate/n-hexane and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)imidazole of m.p. 173°.

Workup

  1. temperaturethe mixture is warmed for an additional 15 minutes
  2. temperatureThe reaction mixture is subsequently cooled in an ice-bath
  3. customthe separated solid is removed by filtration
  4. customAfter separation of the organic phase the aqueous phase
  5. extractionis extracted once with benzene
  6. dry with materialThe combined organic phases are dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crystalline residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-13342ec4c52b45d983b0e298c3d46c3e
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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