Hydrochloric Acid → HCID 86693872, compound

HRID 244074Notes

Reaction equation

HRID 244074 reaction equation
Cl[C:2](=[N:10][N:11]=[C:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[CH3:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:22]=1[NH2:23].CN(C)C1C=CC=CC=1.Cl>ClCCl>[CH3:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]1[N:23]([C:22]2[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:21]=2[CH3:20])[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 68962,6-DimethylanilineHCID 86693871HCID 86693871, compound

Product 1

HCID 86693872HCID 86693872, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

First, 12.6 g (43.3 mmol) of N-[1-chloro-1-(2-methylphenyl)methylidene]-N′-[1-chloro-(1-phenyl)methylidene]hydrazine, 15.7 g (134.5 mmol) of 2,6-dimethylaniline, and 100 ml of N,N-dimethylaniline were put into a 500-ml recovery flask and heated and stirred at 120° C. for 20 hours. After reaction for the predetermined time, this reacted solution was slowly added to 200 ml of 1N hydrochloric acid. Dichloromethane was added to this solution and an objective substance was extracted to an organic layer. The obtained organic layer was washed with water and an aqueous solution of sodium hydrogen carbonate, and was dried with magnesium sulfate. The magnesium sulfate was removed by gravity filtration, and the obtained filtrate was concentrated to give a black liquid. This liquid was purified by silica gel column chromatography. A mixed solvent of ethyl acetate and hexane in a ratio of 1:5 was used as a developing solvent. The obtained fraction was concentrated to give a white solid. This solid was recrystallized with ethyl acetate to give 4.5 g of a white solid of Hmpptz-dmp in a yield of 31%. A synthesis scheme of Step 1 is shown below.

Workup

  1. temperatureheated
  2. customAfter reaction for the predetermined time
  3. extractionan objective substance was extracted to an organic layer
  4. washThe obtained organic layer was washed with water
  5. dry with materialan aqueous solution of sodium hydrogen carbonate, and was dried with magnesium sulfate
  6. customThe magnesium sulfate was removed by gravity filtration
  7. concentrationthe obtained filtrate was concentrated
  8. customto give a black liquid
  9. customThis liquid was purified by silica gel column chromatography
  10. concentrationThe obtained fraction was concentrated
  11. customto give a white solid
  12. customThis solid was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-faa5baa0a572421e97b189390ba2f720
Source dataset
uspto-grants-2014_02
Patent number
US08653553B2

Reaction notes

Loading…