1-Chloro-2,4-Dinitrobenzene → 3-Carbamoyl-1-(2,4-dinitrophenyl)pyridin-1-ium chloride

HRID 1090002Notes

Reaction equation

HRID 1090002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14]([NH2:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.CO>C(OCC)C>[Cl-:1].[C:14]([C:15]1[CH:16]=[N+:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])[CH:18]=[CH:19][CH:20]=1)(=[O:21])[NH2:22]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 887MethanolHCID 936Nicotinamide

Product 1

HCID 127917873-Carbamoyl-1-(2,4-dinitrophenyl)pyridin-1-ium chlorideYield 69.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 20 g (98.7 mmol) of 1-chloro-2,4-dinitrobenzene and 8 g (65.5 mmol) of nicotinamide was gradually heated to 100° C., then stirred at that temperature for one hour. The mixture was cooled to ambient temperature and 100 mL of anhydrous methanol were added. The resultant solution was poured into 400 mL of anhydrous ethyl ether, with vigorous stirring. The solvent was removed by decantation and the residual precipitate was dissolved in 100 mL of methanol. The resultant solution was poured into 400 mL of anhydrous ethyl ether, the solvent was again removed by decantation and the solid residue was dissolved in 200 mL of water. The aqueous solution was refluxed with active charcoal for 30 minutes, then filtered. The filtrate was evaporated and dried in vacuo over phosphorus pentoxide to give 14.7 g (69.2%) of the title compound of the formula ##STR83##

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe solvent was removed by decantation
  3. dissolutionthe residual precipitate was dissolved in 100 mL of methanol
  4. additionThe resultant solution was poured into 400 mL of anhydrous ethyl ether
  5. customthe solvent was again removed by decantation
  6. dissolutionthe solid residue was dissolved in 200 mL of water
  7. temperatureThe aqueous solution was refluxed with active charcoal for 30 minutes
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-c5715e3a7f6748559a091209f48b4166
Source dataset
uspto-grants-1992_01
Patent number
US05079366

Reaction notes

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