Potassium Carbonate → HCID 54322742, compound

HRID 850244Notes

Reaction equation

HRID 850244 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+]([O-])=O)[C:4]=1[C:12]#[N:13])#[N:2].[C:14]([C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:19]=2)[C:4]=1[C:12]#[N:13])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 1626521,2-Benzenedicarbonitrile, 3-nitro-

Product 1

HCID 54322742HCID 54322742, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-dicyano-3-nitrobenzene (1.73 g) and 3-tert-butyl-hydroxybenzene (4.50 g) were allowed to react with each other at 80° C. for 2 hours in dimethylformamide (DMF, 5 ml) with the addition of K2CO3 (5.0 g). After the completion of the reaction, the reaction product was extracted twice with a mixed solvent of water and ethyl acetate (at a volumetric ratio of 1/1), and the layer extracted with ethyl acetate was dried overnight with the use of MgSO4, followed by removal of ethyl acetate by distillation. The residues were isolated and purified by silica gel column chromatography using chloroform to obtain 2.21 g of 1,2-dicyano-3-(3-tert-butylphenyloxy) benzene in a 80% yield.

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction product was extracted twice with a mixed solvent of water and ethyl acetate (at a volumetric ratio of 1/1), and the layer
  3. extractionextracted with ethyl acetate
  4. dry with materialwas dried overnight with the use of MgSO4
  5. customfollowed by removal of ethyl acetate by distillation
  6. customThe residues were isolated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c3e8b429dbbb44de8da66d1c524a4e39
Source dataset
uspto-grants-2000_01
Patent number
US06017604

Reaction notes

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