Potassium Carbonate → HCID 66712849, compound

HRID 523808Notes

Reaction equation

HRID 523808 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[N:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:14]1[CH:19]=[CH:18][C:17]([S:20][C:4]2[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=2)[C:8]#[N:9])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-HCID 178418431pyridine-4-thiol

Product 1

HCID 66712849HCID 66712849, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-nitro-phthalonitrile (17.28 g), pyridine-4-thiol (10.68 g) and potassium carbonate (25.17 g) in N,N-dimethyl-formamide (160 ml) was heated to 85 C and stirred for 3 h. After cooling, the reaction mixture was filtered through a pad of celite and rinsed with ethyl acetate. Filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (eluting with 15-30% of ethyl acetate in methylene chloride) to give the title compound 13.29 g. 1H NMR (200 MHz, CDCl3) δ 8.59 (d, J=6.2 Hz, 2H), 7.68 (m, 3H), 7.24 (d, J=6.3 Hz, 2H).

Workup

  1. temperaturewas heated to 85 C
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered through a pad of celite
  4. washrinsed with ethyl acetate
  5. concentrationFiltrate was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (eluting with 15-30% of ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-defd3f21088e4f64a68fefd9b24c3ec4
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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