Benzenamine hydrochloride (1:1) → HCID 1284736, compound

HRID 2301659Notes

Reaction equation

HRID 2301659 reaction equation
[C:1]1([N:7]=[C:8]([CH2:10][C:11](=O)[CH3:12])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:1]1([NH:7][C:8](=[CH:10][C:11](=[N:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:12])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8870Benzenamine hydrochloride (1:1)HCID 7787544-(phenylimino)-2-pentanone

Product 1

HCID 1284736HCID 1284736, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Then, 605 g of 2-phenylimino-4-pentanone solid and 449 g of anilinehydrochloride were dissolved in 2000 ml of ethanol, and the solution was refluxed for 2 hours. After the solution was cooled at the room temperature, green solid was precipitated. The green solid was separated and dried under vacuum pumping. Then the solid was suspended in 1000 ml of diethylether, and 150 g of NaOH solution in 1200 ml of water was added. The slurry mixture was, then, stirred for 1 hour at the room temperature. Then an organic layer was separated and dried over MgSO4. The solid was filtrated, and solvents were removed by vacuum pumping to get green solid. The green solid was recrystallized to get 650 g of solid (yield=75%). NMR analysis confirmed the structure; 1H-NMR(CDCl3) δ1.95(s, 2CH3), 4.93(s,═CH), 7.02(m, Ph), 7.31(m, Ph), and 13.2(brs, NH).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customwas precipitated
  3. customThe green solid was separated
  4. customdried under vacuum
  5. addition150 g of NaOH solution in 1200 ml of water was added
  6. customThen an organic layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationThe solid was filtrated
  9. customsolvents were removed by vacuum
  10. customto get green solid
  11. customThe green solid was recrystallized

Sources & evidence

ORD record
ord-6934c6fc7ca14d96a9278bee07c6a721
Source dataset
uspto-grants-2002_12
Patent number
US06500906B1

Reaction notes

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