Phenacyl bromide → HCID 53911750, compound

HRID 362303Notes

Reaction equation

HRID 362303 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([NH:22][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:2](=[O:3])[CH3:1])[CH:23]=[CH:24][CH:25]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 928923-Benzyloxyaniline

Product 1

HCID 53911750HCID 53911750, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g of phenacyl bromide and 11 g of 3-benzyloxyaniline are stirred at 60° C. for 2 h in 100 ml of ethanol in the presence of 11.7 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-benzyloxyphenylamino)acetophenone being obtained.

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-1cb685a58f5f443480e53bb64814554b
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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