N,N-dimethyl-p-phenylenediamine → HCID 68154733, compound

HRID 1020015Notes

Reaction equation

HRID 1020015 reaction equation
CO[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]([O:9]C)=O.[CH3:15][N:16]([CH3:24])[C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>CN(C=O)C>[CH3:15][N:16]([CH3:24])[C:17]1[CH:23]=[CH:22][C:20]([N:21]2[C:7](=[O:9])[CH:6]=[CH:5][C:4]([C:11]([O:13][CH3:14])=[O:12])=[CH:3]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 71338068Dimethyl 4-(methoxymethylidene)pent-2-enedioate

Product 1

HCID 68154733HCID 68154733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

After 1.24 g (6.1 mmol) of dimethyl 4-(methoxymethylene)2-pentenedioate obtained in Example 1-1 was dissolved in 10 mL of DMF, 830 g (6.1 mmol) of 4-dimethylaminoaniline was added to the solution. Afterward, the resulting reaction solution was stirred under reflex at about 50° C. for about 3 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo and was then washed using brine, followed by drying using magnesium sulfate and filtration. After distillation under reduced pressure, the resulting product was purified using column chromatography (hexane:ethyl acetate=1:1) to obtain a target compound (Actual yield: 357 mg, Yield ratio: 21%).

Workup

  1. customAfterward, the resulting reaction solution
  2. customthe solvent was removed in vacuo
  3. washwas then washed
  4. customby drying
  5. filtrationmagnesium sulfate and filtration
  6. distillationAfter distillation under reduced pressure
  7. customthe resulting product was purified
  8. customto obtain
  9. customa target compound (Actual yield: 357 mg, Yield ratio: 21%)

Sources & evidence

ORD record
ord-e702e65d08a74266a6baf9ced7c06115
Source dataset
uspto-grants-2014_05
Patent number
US08716309B2

Reaction notes

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