Hydrochloric Acid → HCID 86693872, compound

HRID 2174152Notes

Reaction equation

HRID 2174152 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 a predetermined time, this reaction solution was slowly added to 200 mL of 1N hydrochloric acid. Dichloromethane was added to this solution and a target 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 from ethyl acetate to give 4.5 g of a white solid of Hmpptz-dmp in a yield of 31%. A synthetic scheme of Step 1 is shown below.

Workup

  1. temperatureheated
  2. customAfter reaction for a predetermined time
  3. extractiona target 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 from ethyl acetate

Sources & evidence

ORD record
ord-2359be789aac4a038f10e1a3285e7b3d
Source dataset
uspto-grants-2015_06
Patent number
US09059411B2

Reaction notes

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