Propylenediamine → 5,6-Bis(4-fluorophenyl)-2-methyl-2,3-dihydropyrazine

HRID 1774091Notes

Reaction equation

HRID 1774091 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH:21]([NH2:23])[CH3:22]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:23][CH:21]([CH3:22])[CH2:20][N:19]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6567PropylenediamineHCID 1230724,4'-Difluorobenzil

Product 1

HCID 575436185,6-Bis(4-fluorophenyl)-2-methyl-2,3-dihydropyrazineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, with ethanol as a solvent, 5.31 g of 4,4′-difluorobenzil (by Tokyo Chemical Industry Co., Ltd.) and 1.60 g of 1,2-diaminopropane (by Kanto Chemical Co., Inc.) are mixed. Subsequently, the mixed solution is refluxed for three hours. Then, after the refluxed solution is condensed by using an evaporator and treated with ethanol and then recrystallized, 2,3-bis(4-fluorophenyl)-5-methyl-5,6-dihydropyrazine is obtained (light yellow powder, yield: 86%).

Workup

  1. temperatureSubsequently, the mixed solution is refluxed for three hours
  2. customcondensed
  3. customan evaporator
  4. additiontreated with ethanol
  5. customrecrystallized

Sources & evidence

ORD record
ord-2a50b7f71818437399403a4ab071e283
Source dataset
uspto-grants-2016_02
Patent number
US09257657B2

Reaction notes

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