Phenacyl bromide → HCID 54030800, compound

HRID 362301

Reaction equation

HRID 362301 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH3:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH2:12]([O:13][C:14]1[CH:15]=[C:16]([NH:20][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:2](=[O:3])[CH3:1])[CH:17]=[CH:18][CH:19]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 121203-Ethoxyaniline

Product 1

HCID 54030800HCID 54030800, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g of phenacyl bromide and 3.78 g of m-phenetidine are stirred at 50° C. for 2.5 h in 50 ml of ethanol in the presence of 5.85 g of powdered Na2CO3. The mixture is then cooled and concentrated in an RE. The residue is partitioned between water and methylene chloride and the aqueous phase is extracted twice with methylene chloride. The combined organic phases are dried over Na2SO4 and concentrated. The residue is slurried with ether and the crystals are filtered off, 2'-(3-ethoxyphenylamino)acetophenone being obtained. Further product is again obtained from the mother liquor after addition of petroleum ether.

Workup

  1. temperatureThe mixture is then cooled
  2. concentrationconcentrated in an RE
  3. customThe residue is partitioned between water and methylene chloride
  4. extractionthe aqueous phase is extracted twice with methylene chloride
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. concentrationconcentrated
  7. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-a4c2f8e276d2461884398f346404e01b
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Linked notes

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