2-Bromopropiophenone → HCID 15871299, compound

HRID 565442Notes

Reaction equation

HRID 565442 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-e091fd8c0b91452cb1b58d0213d3415b
Source dataset
uspto-grants-2001_01
Patent number
US06172102B2

Reaction notes

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