Acetic Acid → HCID 21071749, compound

HRID 1372476Notes

Reaction equation

HRID 1372476 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](=O)[CH2:6]Br.[NH2:12][C:13]([NH2:15])=[O:14].C([O-])(=O)C.[NH4+].C(O)(=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:12][C:13](=[O:14])[NH:15][CH:6]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1176UreaHCID 517165Ammonium AcetateHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Product 1

HCID 21071749HCID 21071749, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-bromophenacyl bromide (0.5 g, 1.8 mmol), urea (0.32 g, 5.3 mmol), and ammonium acetate (0.40 g, 5.4 mmol) in water (10 mL) was added glacial acetic acid (0.32 g, 5.4 mmol). The reaction mixture was heated at reflux overnight. After cooling to room temperature, the mixture was extracted with three portions of ethyl acetate, and the combined extracts were dried (magnesium sulfate) and concentrated under reduced pressure to give a brown residue which was triturated with diethyl ether to afford the desired product. LC/MS 238.9 and 240.9 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionthe mixture was extracted with three portions of ethyl acetate
  4. dry with materialthe combined extracts were dried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown residue which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-9d6ca8c58ba142a28ad2b665c312a77b
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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