Propylenediamine → HCID 57543611, compound

HRID 336072Notes

Reaction equation

HRID 336072 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=O)=O)=[CH:5][CH:4]=1.[NH2:25][CH2:26][CH:27]([NH2:29])[CH3:28]>C(O)C>[CH3:28][CH:27]1[CH2:26][N:25]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:24])([F:23])[F:1])=[CH:4][CH:5]=2)[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[N:29]1

Participants

4

Reactant 2

HCID 6567PropylenediamineHCID 5993781,2-bis[4-(trifluoromethyl)phenyl]ethane-1,2-dione

Product 1

HCID 57543611HCID 57543611, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, with 150 mL of dehydrated ethanol as a solvent, 5.07 g of 4,4′-bis(trifluoromethyl)benzil and 1.09 g of 1,2-diaminopropane were mixed, and the mixture was refluxed in a nitrogen atmosphere for four hours. After reaction, a reaction solution was condensed under reduced pressure, and an obtained residue was recrystallized by using ethanol to obtain 2-methyl-5,6-bis(4-trifluoromethylphenyl)-2,3-dihydropyrazine (light yellow crystal, yield: 87%). Further, with 100 mL of dehydrated ethanol as a solvent, 5.05 g of 2-methyl-5,6-bis(4-trifluoromethylphenyl)-2,3-dihydropyrazine that is obtained as described above and 4.26 g of iron (III) chloride were mixed, and the mixture was heated in a nitrogen atmosphere for two hours in a gentle manner. After reaction, water was added into a reaction solution for dilution, and extraction was performed with ether. An extraction solution was dried with magnesium sulfate and filtered, and solvent of filtrate was removed. An obtained residue was recrystallized with ethanol to obtain 5-methyl-2,3-bis(4-trifluoromethylphenyl)pyrazine (CF3DPPR-Me) that is a ligand (white powder, yield: 52%). A synthesis scheme (h-1) relating to the synthesis of Step 1 is shown below.

Workup

  1. temperaturethe mixture was refluxed in a nitrogen atmosphere for four hours
  2. customAfter reaction
  3. customcondensed under reduced pressure
  4. customan obtained residue was recrystallized

Sources & evidence

ORD record
ord-20505feea1a14460b24262a0134caf61
Source dataset
uspto-grants-2014_11
Patent number
US08889266B2

Reaction notes

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