M-Phenylenediamine → HCID 22674043, compound

HRID 1005671Notes

Reaction equation

HRID 1005671 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[CH3:9][CH2:10][O:11][C:12]([CH2:14][C:15]([C:17](OCC)=O)=O)=[O:13].P(Cl)(Cl)([Cl:24])=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:7][C:3]1[CH:2]=[C:1]2[C:6]([C:14]([C:12]([O:11][CH2:10][CH3:9])=[O:13])=[CH:15][C:17]([Cl:24])=[N:8]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7935M-PhenylenediamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 66951Diethyl oxalacetate

Product 1

HCID 22674043HCID 22674043, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 25 g (231 mmol) of m-phenylenediamine was added 43 g (231 mmol) of diethyl oxaloacetate, followed by stirring at 160 degrees for 1 hour. After standing to cool, the crystals were washed with methanol. To a solution of the crystals (3.0 g, 13 mmol) in chloroform (30 ml) was added phosphorus oxychloride (3.6 ml), followed by heating under reflux for 1 hour. After standing to cool, the reaction mixture was poured onto ice water, basified with 1 N sodium hydroxide aqueous solution, and the resulting crystals were collected by filtration. The crystals were washed with tetrahydrofuran and the filtrate was evaporated, to give 4.85 g of the title compound.

Workup

  1. temperatureto cool
  2. washthe crystals were washed with methanol
  3. temperatureby heating
  4. temperatureunder reflux for 1 hour
  5. temperatureto cool
  6. additionthe reaction mixture was poured onto ice water
  7. filtrationthe resulting crystals were collected by filtration
  8. washThe crystals were washed with tetrahydrofuran
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a9cf8abb335e4d9eaf67514f6fff8903
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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