Potassium Carbonate → HCID 66712589, compound

HRID 1866426Notes

Reaction equation

HRID 1866426 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N+]([C:11]1[CH:12]=[C:13]([C:19]#[N:20])[C:14](=[CH:17][CH:18]=1)[C:15]#[N:16])([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[S:1][C:11]1[CH:12]=[C:13]([C:19]#[N:20])[C:14](=[CH:17][CH:18]=1)[C:15]#[N:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-HCID 178418616HCID 178418616, compound

Product 1

HCID 66712589HCID 66712589, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g of 2-mercaptopyridine, 14.2 g of 4-nitrophthalonitrile, and 22.6 g of potassium carbonate were suspended in 250 ml of acetone and heated at reflux temperature for 4 hours. The solution was filtered through a pad of celite and a course glass filter to remove residual solids. The solution was concentrated to a crude residue and purified by column chromatography on silica gel eluting the product with a gradient of 0-10% ethyl acetate in dichloromethane. 6.4 g of product was recovered; 1H NMR (200 Mz, CDCl3) δ=8.49-8.53 (m, 1H), 7.84-7.83 (dd, 1H), 7.76-7.71 (m, 2H), 7.68-7.64 (dd, 1H), 7.40-7.36 (dt, 1H), 7.27-7.20 (m, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 4 hours
  3. filtrationThe solution was filtered through a pad of celite
  4. filtrationa course glass filter
  5. customto remove residual solids
  6. concentrationThe solution was concentrated to a crude residue
  7. custompurified by column chromatography on silica gel eluting the product with a gradient of 0-10% ethyl acetate in dichloromethane
  8. custom6.4 g of product was recovered

Sources & evidence

ORD record
ord-3c9b70933ff6431588eda1674304e721
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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