Aluminum → 1-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]ethanone

HRID 1461432Notes

Reaction equation

HRID 1461432 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[O:22])[CH2:18]S(C)=O.[Al]>O.O1CCCC1>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[O:22])[CH3:18]

Participants

4

Reactant 2

HCID 5359268AluminumHCID 150273821-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]-2-(methylsulfinyl)ethanone

Product 1

HCID 150273831-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]ethanoneYield 60.6%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

1-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]-2-(methylsulfinyl)ethanone (2.0 g, 5.61 mmol) is dissolved in 100 ml of 10% water/tetrahydrofuran and cooled to 0° C. in an ice bath. Aluminum amalgam is prepared by addition of aluminum foil (1.5 g, 56.1 mmol) to 350 ml of 2% aqueous mercuric chloride. After 15 seconds, the liquid is decanted, and the foil is washed twice with absolute ethanol followed by tetrahydrofuran. The freshly prepared aluminum amalgam is added to the reaction mixture which is then stirred for 30 minutes at 0° C. The reaction mixture is filtered through celite, and the solids are washed with tetrahydrofuran. The filtrate is evaporated, and the residue is taken up in ether. The ether solution is washed with 100 ml of water and dried over magnesium sulfate. Evaporation of the solvent gives a yellow solid which is recrystallized from diethyl ether/hexane. Yield (1.0 g, 60%) of 1-[2-[(2,6-dichloro-3 -methylphenyl)amino]phenyl]ethanone; mp 122°-125° C.

Workup

  1. customthe liquid is decanted
  2. washthe foil is washed twice with absolute ethanol
  3. additionThe freshly prepared aluminum amalgam is added to the reaction mixture which
  4. filtrationThe reaction mixture is filtered through celite
  5. washthe solids are washed with tetrahydrofuran
  6. customThe filtrate is evaporated
  7. washThe ether solution is washed with 100 ml of water
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation of the solvent
  10. customgives a yellow solid which
  11. customis recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-397f8b3395ea44d4b627c7025e6f5acd
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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