2-Bromopropiophenone → HCID 15871299, compound

HRID 610043Notes

Reaction equation

HRID 610043 reaction equation
[C:1]([CH2:4][C:5]([NH2:7])=[NH:6])(=[O:3])[NH2:2].Br[CH:9]([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O>C(O)C>[NH2:6][C:5]1[NH:7][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:9]([CH3:18])[C:4]=1[C:1](=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 164522-BromopropiophenoneHCID 413165HCID 413165, compound

Product 1

HCID 15871299HCID 15871299, compoundYield 4.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution (20 ml) of carbamoylacetamidine (5.1 g) in ethanol was added a solution of 2-bromopropiophenone (4.0 g) in ethanol dropwise thereto under ice-cooling with stirring and the mixture was then stirred at room temperature overnight. The insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. The obtained product was washed with benzene, purified by silica gel column chromatography (Wakogel C-200, 200 g; eluent: 50% ethyl acetate/n-hexane), and recrystallized from ethyl acetate/diethyl ether to provide the title compound as colorless crystals (0.2 g). m.p. 195-197° C.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was then stirred at room temperature overnight
  3. filtrationThe insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washThe obtained product was washed with benzene
  6. custompurified by silica gel column chromatography (Wakogel C-200, 200 g; eluent: 50% ethyl acetate/n-hexane)
  7. customrecrystallized from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-ced78a0f3e26474080394b4f79442c8d
Source dataset
uspto-grants-1999_12
Patent number
US05998459

Reaction notes

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