N,N-Dimethylaniline → HCID 59844934, compound

HRID 1056440Notes

Reaction equation

HRID 1056440 reaction equation
Cl[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:3][N:4]=[C:5](Cl)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([N:24]2[C:5]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[N:4][N:3]=[C:2]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 78074-BromoanilineHCID 4528745N-(Chlorophenylmethylene)benzenecarbohydrazonoyl chloride

Product 1

HCID 59844934HCID 59844934, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

4.5 g (16 mmol) of 1,2-bis(chloro(phenyl)methylene)hydrazine, 2.0 g (16 mmol) of 4-bromoaniline, and 30 mL of N,N-dimethylaniline were put into a 100 mL three-neck flask, and nitrogen substitution was performed on the contents of the flask. The mixture was stirred at 135° C. for 5 hours. After the reaction, a solid was precipitated out with the reactive solution being added to approximately 100 mL of 1 N diluted hydrochloric acid and the mixture being stirred for 30 minutes. Suction filtration was performed on the precipitated solid, and a solid was obtained. The obtained solid was dissolved in toluene and washed with water and a saturated sodium carbonate solution, in the order given. Magnesium sulfate was added to an organic layer, and the mixture was dried. Suction filtration was performed on the mixture to remove the magnesium sulfate, and thus a filtrate was obtained. The solid, which was obtained by condensation of the obtained filtrate, was recrystallized with a mixed solvent of ethanol and hexane, so that 2.3 g of a powdery white solid, which was the object of the synthesis, was obtained at a yield of 38%.

Workup

  1. customAfter the reaction
  2. customa solid was precipitated out with the reactive solution
  3. additionbeing added to approximately 100 mL of 1 N diluted hydrochloric acid
  4. stirringthe mixture being stirred for 30 minutes
  5. filtrationSuction filtration
  6. customa solid was obtained
  7. washwashed with water
  8. additionMagnesium sulfate was added to an organic layer
  9. customthe mixture was dried
  10. filtrationSuction filtration
  11. customto remove the magnesium sulfate
  12. customthus a filtrate was obtained
  13. customThe solid, which was obtained by condensation of the obtained filtrate
  14. customwas recrystallized with a mixed solvent of ethanol and hexane, so that 2.3 g of a powdery white solid, which
  15. customthe object of the synthesis
  16. customwas obtained at a yield of 38%

Sources & evidence

ORD record
ord-0d326fa746fb44b09308609fae824f84
Source dataset
uspto-grants-2016_07
Patent number
US09397299B2

Reaction notes

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